NZ618376A - Fuel composition - Google Patents
Fuel composition Download PDFInfo
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- NZ618376A NZ618376A NZ618376A NZ61837612A NZ618376A NZ 618376 A NZ618376 A NZ 618376A NZ 618376 A NZ618376 A NZ 618376A NZ 61837612 A NZ61837612 A NZ 61837612A NZ 618376 A NZ618376 A NZ 618376A
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/32—Liquid carbonaceous fuels consisting of coal-oil suspensions or aqueous emulsions or oil emulsions
- C10L1/328—Oil emulsions containing water or any other hydrophilic phase
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
- C10L2250/08—Emulsion details
- C10L2250/084—Water in oil (w/o) emulsion
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Abstract
Disclosed herein is a fuel composition comprising: (a) a fuel; and (b) a polyglycerol ester of a fatty acid wherein the polyglycerol ester of a fatty acid is present in an amount of no greater than 0.5 weight% based on the total fuel composition; and wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of the polyglycerols. Also disclosed is a method for improving the stability of a fuel composition containing fuel and water using the polyglycerol ester fuel compositions.
Description
FUELCOMPOSITION
The present invention relates to a composition. In particular the present invention relates
to fuel compositions having reduced nitrogen oxide emissions when combusted.
As discussed in US 7,491,247 environmental considerations and government regulations
have increased the need to reduce nitrogen oxide (NOx) production. Nitrogen oxides
comprise a major irritant in smog and are believed to contribute to tropospheric ozone
which is a known threat to health. Relatively high flame temperatures reached in internal
combustion engines, for example diesel-fuelled engines, increase the tendency for the
production of nitrogen oxides (NOx). These are formed from both the combination of
nitrogen and oxygen in the combustion chamber and from the oxidation of organic
nitrogen species in the fuel.
Various methods for reducing NOx production include the use of catalytic converters,
engine timing changes, exhaust recirculation, and the burning of "clean" fuels. These
methods are generally too expensive and/or too complicated to be placed in widespread
use. The rates at which NOx are formed is related to the flame temperature; a small
reduction in flame temperature can result in a large reduction in the production of
nitrogen oxides.
It has been shown that introducing water into the combustion zone can lower the flame
temperature and thus lower NOx production, however; the direct injection of water
requires costly and complicated changes in engine design. Further attempts to use water
to reduce flame temperature include the use of aqueous fuels, i.e., incorporating both
water and fuel into an emulsion. Problems that may occur from long-term use of aqueous
fuels include precipitate depositions include coalescing ionic species resulting in filter
plugging and inorganic post combustion deposits resulting in turbo fouling. Another
problem related to aqueous fuel compositions is that they often require substantial
engine modifications, such as the addition of in-line homogenizers, thereby limiting their
commercial utility.
Another method for introducing water into the combustion area is to use fuel emulsions in
which water is emulsified into a fuel continuous phase, i.e., invert fuel emulsions. A
problem with these invert fuel emulsions is obtaining and maintaining the stability of the
emulsion under conventional use conditions. Gravitational phase separation ( during
storage) and high temperature high pressure/shear flow rate phase separation (in a
working engine) of these emulsions present the major hurdle preventing their commercial
use.
DE-A-3229918 teaches the preparation of emulsions of 25 wt. of water in diesel oil using
emulsifier which are polyesters of saturated or unsaturated fatty acids having 8-22
carbon atoms. The emulsifiers include polyglycerol esters, sorbitan esters or
diacetyltartaric acid esters of glycerol esters of the fatty acids. The emulsifiers are dosed
in the fuel compositions in amounts of 0.65 to 1.6 wt.%. The diesel emulsions are taught
to be stable for at least 6 months and, as compared with pure diesel oil used in engines,
give a better fuel economy, less coke deposition and a lower content of CO and
hydrocarbons in the exhaust gas. In such a system, the emulsifier is potentially the most
expensive component and dosage at the high levels of this document, such as at 1.6
wt.% would be expensive in use and potentially not commercially viable.
The present invention addresses the problems associated with the use of fuel emulsion
compositions by providing a stable fuel emulsion composition with the beneficial
reduction in NOx emissions using commercially viable amounts of emulsifier.
The present invention alleviates the problems of the prior art.
In one aspect the present invention provides a fuel composition comprising:
(a) a fuel; and
(b) a polyglycerol ester of a fatty acid, wherein the polyglycerol ester of a fatty acid is
present in an amount of no greater than 0.5 weight% based on the total fuel composition;
wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises a mixture of
diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the
polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined
weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on
the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0
weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount
of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol
in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the
polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined
weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on
the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0
weight% based on the combined weight of the polyglycerols.
In one aspect the present invention provides a method for improving the stability of a fuel
composition containing (a ) fuel and (c ) water, the method comprising mixing with the fuel
and water, (b) a polyglycerol ester of a fatty acid, wherein the polyglycerol ester of a fatty
acid is present in an amount of no greater than 0.5 weight% based on the total fuel
composition;
wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises a mixture of
diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the
polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined
weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on
the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0
weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount
of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol
in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the
polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined
weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on
the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0
weight% based on the combined weight of the polyglycerols.
In one aspect the present invention provides a kit for preparing a fuel composition as
defined herein, the kit comprising a polyglycerol ester of a fatty acid as described herein;
together with instructions for use to prepare a fuel composition containing fuel and water.
In one aspect the present invention provides use of a polyglycerol ester of a fatty acid for
improving the stability of a fuel composition containing fuel and water;
wherein the polyglycerol ester of a fatty acid is present in an amount of no greater than
0.5 weight% based on the total fuel composition; and
wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises a mixture of
diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the
polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined
weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on
the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0
weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount
of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol
in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the
polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined
weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on
the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0
weight% based on the combined weight of the polyglycerols.
We have shown that when a polyglycerol composition is used which has predominantly
one polyglycerol present, such as diglycerol or triglycerol, then the polyglycerol
composition must be present in a significantly higher amount to provide a fuel/water
emulsion which is stable during storage. In contrast we have surprisingly found that
having a broad range of polyglycerols present in a polyglycerol composition, and in
particular the specific ranges recited herein, then a lower and therefore commercially
viable amount of emulsifiers may be used while still providing a fuel and water emulsion
which is stable over the period required in use, such as 3 hours. The "flat" distribution of
polyglycerols allows for this enhanced effect at low dosages. By flat distribution it is
meant that the polyglycerols contain a broad range of polyglycerols chain lengths and the
broad range of polyglycerols are present in an amount such that only a few polyglycerol
chain lengths dominate the distribution of polyglycerols. For example in a flat distribution
one or two polyglycerol chain lengths do not make up 70 or 80% of the total amount of
polyglycerols.
For ease of reference these and further aspects of the present invention are now
discussed under appropriate section headings. However, the teachings under each
section are not necessarily limited to each particular section.
Composition
As previously mentioned, in one aspect the present invention provides a fuel composition
comprising:
(a) a fuel; and
(b) a polyglycerol ester of a fatty acid;
wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises a mixture of
diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the
polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined
weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on
the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0
weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount
of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol
in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the
polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined
weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on
the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0
weight% based on the combined weight of the polyglycerols.
Polyglycerol Ester of a Fatty Acid
As is understood by one skilled in the art polyglycerol ester of a fatty acid is an emulsifier
comprising a polyglycerol 'backbone' onto which fatty acid side chains are attached.
Polyglycerol esters of fatty acids are typically prepared by polymerisation of glycerol to
provide one or more polyglycerols to which the fatty acids are then attached. The fatty
acids are generally attached by one of two routes. A first route involves the direct
attachment of the fatty acid to the polyglycerol. The second route involves inter-
esterifying a polyglycerol and a triglyceride thereby transferring fatty acids from the
triglyceride to the polyglycerol. The polymerisation of glycerol typically provides a mixture
of polyglycerols of different degrees of polymerisation. The mixture of polyglycerols of
different degrees of polymerisation is described herein as a polyglycerol composition. It
will be understood by one skilled in the art that references to a polyglycerol composition
having particular polyglycerol components requires only that those components be
present in the amount specified. It will be appreciated by one skilled in the art that
because of the nature of polymerisation of glycerol, the polyglycerol composition may
contain other polyglycerols having degrees of polymerisation not recited herein. In
determining the amounts of polyglycerols in the polyglycerol composition, the total
amount of all polyglycerols (irrespective of degree of polymerisation) is determined to
provide the total weight of the polyglycerol composition. Materials which are not a
polyglycerol do not form part of the polyglycerol composition and their weight is not
considered when determining the total weight of the polyglycerol composition.
References in the present specification to "the combined weight of the polyglycerols"
encompass the total combined weight of all polyglycerols, irrespective of their chain
length and irrespective of whether the polyglycerol is recited in the listing of
polyglycerols.
As discussed here in the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight%
based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5
weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount
of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol
in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols;
hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the
polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined
weight of the polyglycerols; octaglycerol in an amount of 3.0 to 12.0 weight% based on
the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0
weight% based on the combined weight of the polyglycerols; decaglycerol in an amount
of 0.0 to 8.0 weight% based on the combined weight of the polyglycerols; and
unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of
the polyglycerols.
It will be appreciated by one skilled in the art that polyglycerols may be either in the form
of a cyclic polyglycerol or an acyclic polyglycerol. Acyclic polyglycerols are straight chain
and branched chain polyglycerols, that is acyclic polyglycerols are formed entirely from
glycerol groups linked such that no rings are formed. Cyclic polyglycerols contain a ring
structure. References in the present specification to a polyglycerol of a particular degree
of polymerisation, for example triglycerol referring to a polyglycerol having a degree of
polymerisation of 3, include both the polyglycerol in cyclic form and in acyclic form. We
have further determined the preferred amounts of cyclic and acyclic polyglycerols for
each of diglycerol, triglycerol, tetraglycerol and pentaglycerol. In one preferred aspect the
diglycerol comprises acyclic diglycerol in an amount of 6.0 to 25.0 weight% based on the
combined weight of the polyglycerols, and cyclic diglycerol in an amount of 5.0 to 13.0
weight% based on the combined weight of the polyglycerols. In one preferred aspect the
triglycerol comprises acyclic triglycerol in an amount of 7.0 to 21.0 weight% based on the
combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5
weight% based on the combined weight of the polyglycerols. In one preferred aspect the
tetraglycerol comprises acyclic tetraglycerol in an amount of 5.5 to 15.0 weight% based
on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5
to 8.0 weight% based on the combined weight of the polyglycerols. In one preferred
aspect the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect
the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 25.0 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
.0 to 13.0 weight% based on the combined weight of the polyglycerols;
the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 21.0 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
2.5 to 9.5 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.5 to 15.0
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 6.0 to
.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in
an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 7.0 to
.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in
an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0
to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 6.0 to
15.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in
an amount of 5.5 to 13.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 7.0 to
.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in
an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0
to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect
the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 15.0 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
.5 to 13.0 weight% based on the combined weight of the polyglycerols
the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 15.0 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
2.5 to 9.5 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0 to 13.0
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect
the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 15.0 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
5.5 to 13.0 weight% based on the combined weight of the polyglycerols
the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 15.0 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
2.5 to 9.5 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0 to 13.0
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 1.0 to 8.0 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 6.0 to 15.0 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 5.5 to 13.0 weight%
based on the combined weight of the polyglycerols
acyclic triglycerol in an amount of 7.0 to 15.0 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 5.0 to 13.0 weight% based on the combined
weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5 to 8.0 weight%
based on the combined weight of the polyglycerols; and
acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight%
based on the combined weight of the polyglycerols.
hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight
of the polyglycerols
heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined
weight of the polyglycerols
octaglycerol in an amount of 4.0 to 12.0 weight% based on the combined weight
of the polyglycerols
nonaglycerol in an amount of 2.0 to 10.0 weight% based on the combined weight
of the polyglycerols
decaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.1 to 7.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 6.0 to 15.0 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 5.0 to 13.0 weight%
based on the combined weight of the polyglycerols
acyclic triglycerol in an amount of 7.0 to 15.0 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 5.0 to 13.0 weight% based on the combined
weight of the polyglycerols, and cyclic tetraglycerol in an amount of 1.0 to 8.0 weight%
based on the combined weight of the polyglycerols; and
acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight%
based on the combined weight of the polyglycerols.
hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight
of the polyglycerols
heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined
weight of the polyglycerols
octaglycerol in an amount of 4.0 to 12.0 weight% based on the combined weight
of the polyglycerols
nonaglycerol in an amount of 2.0 to 10.0 weight% based on the combined weight
of the polyglycerols
decaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.1 to 7.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises diglycerol in an amount of 15.0 to 23.5 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an
amount of 13.5 to 20.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises tetraglycerol in an amount of 10.0 to 17.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in
an amount of 8.0 to 14.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises hexaglycerol in an amount of 8.0 to 11.5 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in
an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises octaglycerol in an amount of 6.5 to 10.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in
an amount of 4.0 to 8.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises decaglycerol in an amount of 1.5 to 6.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises
unadecaglycerol in an amount of 0.5 to 5.0 weight% based on the combined weight of
the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises diglycerol in an amount of 15.0 to 23.5 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises triglycerol in an amount of 13.5 to 20.5 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises tetraglycerol in an amount of 10.0 to 17.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises pentaglycerol in an amount of 8.0 to 14.5 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises hexaglycerol in an amount of 8.0 to 11.5 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises heptaglycerol in an amount of 7.5 to 11.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises octaglycerol in an amount of 6.5 to 10.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises nonaglycerol in an amount of 4.0 to 8.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises decaglycerol in an amount of 1.5 to 6.0 weight% based on the combined
weight of the polyglycerols; and
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises unadecaglycerol in an amount of 0.5 to 5.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 8.0 to
12.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in
an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 9.0 to
13.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in
an amount of 4.5 to 7.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of 7.5
to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 2.5 to 6.0 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 5.0 to 9.0 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect
the diglycerol comprises acyclic diglycerol in an amount of 8.0 to 12.5 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
7.5 to 11.0 weight% based on the combined weight of the polyglycerols;
the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 13.0 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
4.5 to 7.5 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 7.5 to 11.0
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 5.0 to 9.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 8.0 to 12.5 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 7.5 to 11.0 weight%
based on the combined weight of the polyglycerols;
acyclic triglycerol in an amount of 9.0 to 13.0 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 4.5 to 7.5 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 7.5 to 11.0 weight% based on the combined
weight of the polyglycerols, and cyclic tetraglycerol in an amount of 2.5 to 6.0 weight%
based on the combined weight of the polyglycerols; and
acyclic pentaglycerol in an amount of 5.0 to 9.0 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight%
based on the combined weight of the polyglycerols.
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises hexaglycerol in an amount of 8.0 to 11.5 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises heptaglycerol in an amount of 7.5 to 11.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises octaglycerol in an amount of 6.5 to 10.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises nonaglycerol in an amount of 4.0 to 8.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises decaglycerol in an amount of 1.5 to 6.0 weight% based on the combined
weight of the polyglycerols; and
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises unadecaglycerol in an amount of 0.5 to 5.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises diglycerol in an amount of 17.6 to 21.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an
amount of 15.9 to 18.1 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises tetraglycerol in an amount of 12.5 to 14.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in
an amount of 10.5 to 12.2 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises hexaglycerol in an amount of 9.3 to 10.1 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in
an amount of 8.6 to 9.9 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises octaglycerol in an amount of 7.3 to 8.9 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in
an amount of 5.5 to 6.4 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises decaglycerol in an amount of 2.9 to 4.5 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises
unadecaglycerol in an amount of 1.8 to 3.7 weight% based on the combined weight of
the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises diglycerol in an amount of 17.6 to 21.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises triglycerol in an amount of 15.9 to 18.1 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises tetraglycerol in an amount of 12.5 to 14.0 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises pentaglycerol in an amount of 10.5 to 12.2 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises hexaglycerol in an amount of 9.3 to 10.1 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises heptaglycerol in an amount of 8.6 to 9.9 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises octaglycerol in an amount of 7.3 to 8.9 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises nonaglycerol in an amount of 5.5 to 6.4 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises decaglycerol in an amount of 2.9 to 4.5 weight% based on the combined
weight of the polyglycerols; and
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises unadecaglycerol in an amount of 1.8 to 3.7 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 9.1 to
11.4 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in
an amount of 8.5 to 9.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 10.0 to
11.8 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in
an amount of 5.9 to 6.3 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.4
to 9.5 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 4.1 to 4.4 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 6.7 to 7.6 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 3.8 to 4.6 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect
the diglycerol comprises acyclic diglycerol in an amount of 9.1 to 11.4 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
8.5 to 9.5 weight% based on the combined weight of the polyglycerols;
the triglycerol comprises acyclic triglycerol in an amount of 10.0 to 11.8 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
5.9 to 6.3 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.4 to 9.5
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 4.1 to 4.4 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.7 to 7.6
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 3.8 to 4.6 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 9.1 to 11.4 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 8.5 to 9.5 weight%
based on the combined weight of the polyglycerols;
acyclic triglycerol in an amount of 10.0 to 11.8 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 5.9 to 6.3 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 8.4 to 9.5 weight% based on the combined
weight of the polyglycerols, and cyclic tetraglycerol in an amount of 4.1 to 4.4 weight%
based on the combined weight of the polyglycerols; and
acyclic pentaglycerol in an amount of 6.7 to 7.6 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 3.8 to 4.6 weight%
based on the combined weight of the polyglycerols.
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises hexaglycerol in an amount of 9.3 to 10.1 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises heptaglycerol in an amount of 8.6 to 9.9 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises octaglycerol in an amount of 7.3 to 8.9 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises nonaglycerol in an amount of 5.5 to 6.4 weight% based on the combined
weight of the polyglycerols;
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises decaglycerol in an amount of 2.9 to 4.5 weight% based on the combined
weight of the polyglycerols; and
the polyglycerol composition used to form the polyglycerol ester of a fatty acid
comprises unadecaglycerol in an amount of 1.8 to 3.7 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises diglycerol in an amount of 18.0 to 32.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an
amount of 16.0 to 24.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises tetraglycerol in an amount of 12.0 to 16.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in
an amount of 8.0 to 12.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises hexaglycerol in an amount of 7.0 to 11.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in
an amount of 5.0 to 10.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises octaglycerol in an amount of 3.0 to 9.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in
an amount of 1.5 to 7.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises decaglycerol in an amount of 0.0 to 4.5 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises
unadecaglycerol in an amount of 0.0 to 4.0 weight% based on the combined weight of
the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
diglycerol in an amount of 18.0 to 32.0 weight% based on the combined weight
of the polyglycerols;
triglycerol in an amount of 16.0 to 24.0 weight% based on the combined weight
of the polyglycerols;
tetraglycerol in an amount of 12.0 to 16.0 weight% based on the combined
weight of the polyglycerols;
pentaglycerol in an amount of 8.0 to 12.0 weight% based on the combined
weight of the polyglycerols;
hexaglycerol in an amount of 7.0 to 11.0 weight% based on the combined weight
of the polyglycerols;
heptaglycerol in an amount of 5.0 to 10.0 weight% based on the combined
weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 9.0 weight% based on the combined weight
of the polyglycerols;
nonaglycerol in an amount of 1.5 to 7.0 weight% based on the combined weight
of the polyglycerols;
decaglycerol in an amount of 0.0 to 4.5 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.0 to 4.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 9.0 to
24.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in
an amount of 6.5 to 10.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 9.0 to
.5 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in
an amount of 3.5 to 6.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.0
to 13.5 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 2.0 to 4.5 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 6.0 to 9.0 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 2.0 to 5.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect in the polyglycerol composition used to form the polyglycerol
ester of a fatty acid
the diglycerol comprises acyclic diglycerol in an amount of 9.0 o 24.5 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
6.5 to 10.0 weight% based on the combined weight of the polyglycerols;
the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 20.5 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
3.5 to 6.5 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.0 to 13.5
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 2.0 to 4.5 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.0 to 9.0
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 2.0 to 5.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 9.0 to 24.5 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 10.0 weight%
based on the combined weight of the polyglycerols;
acyclic triglycerol in an amount of 9.0 to 20.5 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 3.5 to 6.5 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 8.0 to 13.5 weight% based on the combined
weight of the polyglycerols, and cyclic tetraglycerol in an amount of 2.0 to 4.5 weight%
based on the combined weight of the polyglycerols;
acyclic pentaglycerol in an amount of 6.0 to 9.0 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.0 to 5.0 weight%
based on the combined weight of the polyglycerols;
hexaglycerol in an amount of 7.0 to 11.0 weight% based on the combined weight
of the polyglycerols;
heptaglycerol in an amount of 5.0 to 10.0 weight% based on the combined
weight of the polyglycerols;
octaglycerol in an amount of 3.0 to 9.0 weight% based on the combined weight
of the polyglycerols;
nonaglycerol in an amount of 1.5 to 7.0 weight% based on the combined weight
of the polyglycerols;
decaglycerol in an amount of 0.0 to 4.5 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.0 to 4.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises diglycerol in an amount of 26.0 to 34.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an
amount of 21.0 to 25.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises tetraglycerol in an amount of 12.0 to 17.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in
an amount of 8.0 to 12.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises hexaglycerol in an amount of 6.0 to 10.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in
an amount of 4.5 to 7.5 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises octaglycerol in an amount of 2.5 to 5.5 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in
an amount of 1.0 to 3.0 weight% based on the combined weight of the polyglycerols. In
one preferred aspect the polyglycerol composition used to form the polyglycerol ester of
a fatty acid comprises decaglycerol in an amount of 0.0 to 1.0 weight% based on the
combined weight of the polyglycerols. In one preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid comprises
unadecaglycerol in an amount of 0.0 to 0.5 weight% based on the combined weight of
the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises unadecaglycerol in an amount of 0.0 to 0.01 weight% based on
the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
diglycerol in an amount of 26.0 to 34.0 weight% based on the combined weight
of the polyglycerols;
triglycerol in an amount of 21.0 to 25.0 weight% based on the combined weight of
the polyglycerols;
tetraglycerol in an amount of 12.0 to 17.0 weight% based on the combined weight
of the polyglycerols;
pentaglycerol in an amount of 8.0 to 12.0 weight% based on the combined weight
of the polyglycerols;
hexaglycerol in an amount of 6.0 to 10.0 weight% based on the combined weight
of the polyglycerols;
heptaglycerol in an amount of 4.5 to 7.5 weight% based on the combined weight
of the polyglycerols;
octaglycerol in an amount of 2.5 to 5.5 weight% based on the combined weight of
the polyglycerols;
nonaglycerol in an amount of 1.0 to 3.0 weight% based on the combined weight
of the polyglycerols;
decaglycerol in an amount of 0.0 to 1.0 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.0 to 0.5 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the diglycerol comprises acyclic diglycerol in an amount of 20.0
to 26.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol
in an amount of 6.5 to 8.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 18.0
to 21.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol
in an amount of 2.5 to 5.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the tetraglycerol comprises acyclic tetraglycerol in an amount of
11.0 to 14.5 weight% based on the combined weight of the polyglycerols, and cyclic
tetraglycerol in an amount of 1.5 to 4.0 weight% based on the combined weight of the
polyglycerols. In one preferred aspect the pentaglycerol comprises acyclic pentaglycerol
in an amount of 6.5 to 9.5 weight% based on the combined weight of the polyglycerols,
and cyclic pentaglycerol in an amount of 1.5 to 4.0 weight% based on the combined
weight of the polyglycerols.
In one preferred aspect the triglycerol comprises acyclic triglycerol in an amount of 18.0
to 21.0 weight% based on the combined weight of the polyglycerols,
In one preferred aspect in the polyglycerol composition used to form the polyglycerol
ester of a fatty acid
the diglycerol comprises acyclic diglycerol in an amount of 20.0 to 26.0 weight%
based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of
6.5 to 8.0 weight% based on the combined weight of the polyglycerols;
the triglycerol comprises acyclic triglycerol in an amount of 18.0 to 21.0 weight%
based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of
2.5 to 5.0 weight% based on the combined weight of the polyglycerols;
the tetraglycerol comprises acyclic tetraglycerol in an amount of 11.0 to 14.5
weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in
an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols; and
the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.5 to 9.5
weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in
an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid comprises a mixture of
acyclic diglycerol in an amount of 20.0 to 26.0 weight% based on the combined
weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 8.0 weight%
based on the combined weight of the polyglycerols;
acyclic triglycerol in an amount of 18.0 to 21.0 weight% based on the combined
weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 5.0 weight%
based on the combined weight of the polyglycerols;
acyclic tetraglycerol in an amount of 11.0 to 14.5 weight% based on the
combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 1.5 to 4.0
weight% based on the combined weight of the polyglycerols;
acyclic pentaglycerol in an amount of 6.5 to 9.5 weight% based on the combined
weight of the polyglycerols, and cyclic pentaglycerol in an amount of 1.5 to 4.0 weight%
based on the combined weight of the polyglycerols;
hexaglycerol in an amount of 6.0 to 10.0 weight% based on the combined weight
of the polyglycerols;
heptaglycerol in an amount of 4.5 to 7.5 weight% based on the combined weight
of the polyglycerols;
octaglycerol in an amount of 2.5 to 5.5 weight% based on the combined weight of
the polyglycerols;
nonaglycerol in an amount of 1.0 to 3.0 weight% based on the combined weight
of the polyglycerols;
decaglycerol in an amount of 0.0 to 1.0 weight% based on the combined weight
of the polyglycerols; and
unadecaglycerol in an amount of 0.0 to 0.5 weight% based on the combined
weight of the polyglycerols.
The fatty acid side chains attached to the polyglycerol may be of any suitable length. The
polyglycerol ester of a fatty acid may be a polyglycerol ester of a single fatty acid, or
polyglycerol ester of a mixture of fatty acids. The fatty chain lengths of the fatty acids of
the polyglycerol ester need not be of the same length. Typically the polyglycerol ester of
a fatty acid is an ester of a fatty acid of a C12 to C22 fatty acid. Preferably the
polyglycerol ester of a fatty acid is an ester of a C16 or C22 fatty acid. Preferably the
polyglycerol ester of a fatty acid is an ester of a C16 or C18 fatty acid. Preferably the
polyglycerol ester of a fatty acid is an ester of a C18 fatty acid.
The fatty acid of the polyglycerol ester of a fatty acid may be saturated fatty acid,
unsaturated fatty acid or a mixture of saturated fatty acid and unsaturated fatty acid. In
one aspect the fatty acid of the polyglycerol ester of a fatty acid is an unsaturated fatty
acid. The fatty acid of the polyglycerol ester of a fatty acid may be mono- or di-
unsaturated fatty acid. Preferably the fatty acid of the polyglycerol ester of a fatty acid is
a mono-unsaturated fatty acid.
A highly preferred fatty acid of the polyglycerol ester of a fatty acid is oleic acid ((9Z)-
Octadecenoic acid).
The fatty acids attached to the polyglycerol may be provided from any suitable source.
Thus in one aspect, the polyglycerol fatty acid ester is prepared from fatty acids from oils
selected from rape seed oil, high oleic rape seed oil, soy oil, high oleic sunflower oil, tall
oil and mixtures thereof.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid has a hydroxyl value of from 880 to 1230 mg KOH/g. In one preferred
aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid
has a hydroxyl value of from 1130 to 1230 mg KOH/g. In one preferred aspect the
polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl
value of from 880 to 1060 mg KOH/g. In a further preferred aspect the polyglycerol
composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of
from 950 to 990 mg KOH/g.
In one preferred aspect the polyglycerol composition used to form the polyglycerol ester
of a fatty acid has a refractive index at 50 C of from 1.4860 to 1.4925. In one preferred
aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid
has a refractive index at 50 C of from 1.4895 to 1.4925. In a further preferred aspect the
polyglycerol composition used to form the polyglycerol ester of a fatty acid has a
refractive index at 50 C of from 1.4900 to 1.4920. In a further preferred aspect the
polyglycerol composition used to form the polyglycerol ester of a fatty acid has a
refractive index at 50 C of from 1.4900 to 1.4910. In one preferred aspect the
polyglycerol composition used to form the polyglycerol ester of a fatty acid has a
refractive index at 25 C of from 1.4855 to 1.4935.
In one preferred aspect the polyglycerol ester of a fatty acid has a viscosity of less than
700 mPa s at 20°C, such as less than 600 mPa s at 20°C, such as less than 500 mPa s
at 20°C, such as less than 400 mPa s at 20°C, such as less than 350 mPa s at 20°C,
such as less than 300 mPa s at 20°C, such as less than 250 mPa s at 20°C, such as
less than 200 mPa s at 20°C. We have found that during the preparation of a fuel
emulsion in accordance with the present invention a low viscosity, such as that described
above, and preferably less than 200 mPa s at 20°C, is an important factor in the
preparation of an effective emulsion.
We have found that a means by which the viscosity the polyglycerol ester of a fatty acid
may be controlled is by control of the ratio of the polyol to triglyceride source when
preparing the present polyglycerol ester of a fatty acid, as well as the fatty acid profile
which is described in detail herein. The effect of ratio of the polyol to triglyceride source
is shown in Figure 8. Thus in one aspect the polyglycerol ester of a fatty acid is prepared
by reacting a polyglycerol and a fatty acid triglyceride in a ratio of polyglycerol to fatty
acid triglyceride of from 1:1 to 1:10. Preferably the polyglycerol ester of a fatty acid is
prepared by reacting a polyglycerol and a fatty acid triglyceride in a ratio of polyglycerol
to fatty acid triglyceride of from 1:1 to 1:9, such as from 1:1 to 1:8, such as from 1:1 to
1:7, such as from 1:1 to 1:6, such as from 1:1 to 1:5, such as from 1:1 to 1:4, such as
from 1:2 to 1:4, such as from 1:2 to 1:3, such as approximately 1:2.8, such as from 1:4 to
1:9, such as from 1:4 to 1:8, such as from 1:4 to 1:7, such as from 1:4 to 1:6, such as
from 1:4 to 1:5, such as from 1:5 to 1:7, such as from 1:6 to 1:7, such as approximately
1:6.7.
Fuel Composition
When a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as
described herein is provided in accordance with the present invention, the polyglycerol
ester may be dosed in the water and fuel composition in any suitable amount to provide
an emulsion of desired stability. In one aspect the fuel composition comprises a
polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described
herein in an amount of from 0.1 to 2.0 wt.% based on the total fuel composition. In a
further aspect the fuel composition comprises a polyglycerol ester of a fatty acid
prepared from a mixture of polyglycerols as described herein in an amount of from 0.1 to
1.0 wt.% based on the total fuel composition. In a further aspect the fuel composition
comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as
described herein in an amount of from 0.1 to 0.5 wt.% based on the total fuel
composition. In a further aspect the fuel composition comprises a polyglycerol ester of a
fatty acid prepared from a mixture of polyglycerols as described herein in an amount of
less than 0.5 wt.% based on the total fuel composition. In a further aspect the fuel
composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of
polyglycerols as described herein in an amount of less than 0.3 wt.% based on the total
fuel composition. In a further aspect the fuel composition comprises a polyglycerol ester
of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount
of less than 0.25 wt.% based on the total fuel composition. In a further aspect the fuel
composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of
polyglycerols as described herein in an amount of less than 0.2 wt.% based on the total
fuel composition. In a further aspect the fuel composition comprises a polyglycerol ester
of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount
of less than 0.15 wt.% based on the total fuel composition. In a further aspect the fuel
composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of
polyglycerols as described herein in an amount of less than 0.1 wt.% based on the total
fuel composition.
As discussed herein we have identified that by use of the "flat" composition of
polyglycerols the emulsifier may be used in lower amounts than required in the prior art.
Thus in the preferred aspect the polyglycerol ester of a fatty acid is present in an amount
of less than 0.5 wt.%. The improved activity of the composition of polyglycerol esters of
the present invention allows for the emulsifier to be dosed at lower amounts than had
previously been required in the prior art. This is advantageous both for reasons of cost
and also for storage. These materials are dosed in use and therefore must be
transported by the user. Minimising the amount of material required to achieve the
desired effect is important for end users. Although the present composition allows for use
at lower levels than the prior art, the present composition may be dosed at any level, for
example it may be dosed at a higher level in a demanding application. It is appreciated
by one skilled in the art that depending on the required use and stability time desired the
polyglycerol ester of a fatty acid may be dosed at any amount.
Fuel
As discussed herein, the emulsifiers described allow for the preparation of an emulsion
of fuel and water. A fuel suitable for preparing into an emulsion but which has yet to be
combined with water is hereby encompassed within the present invention. However, in a
preferred aspect, the fuel containing the emulsifiers is combined with water and the fuel
composition further comprises (c) water. It will be appreciated that in this aspect the fuel
composition may be prepared by first dosing the polyglycerol ester of a fatty acid into the
fuel, such as marine gasoil (MGO), after which water is dosed into the fuel/emulsifier
blend.
The amount of water may be selected based on the requirements of the combustion
system. In one aspect the fuel composition further comprises (c) water in an amount of
from 10 to 70 wt.% based on the total fuel composition. Preferably the water is present in
an amount of from 30 to 60 wt.% based on the total fuel composition. Preferably the
water is present in an amount of from 33 to 50 wt.% based on the total fuel composition.
The composition according to the present invention may comprise one or more additives
for example, to improve various aspects of the fuel to which the composition is typically
added or to improve various aspects of the combustion system performance. Suitable
additional additives include detergents, carrier oils, anti-oxidants, corrosion inhibitors,
colour stabilisers, metal deactivators, cetane number improvers, other combustion
improvers, antifoams, pour point depressants, cold filter plugging point depressants, wax
anti-settling additives, dispersants, deodorants, dyes, smoke suppressants, lubricity
agents, and other particulate filter regeneration additives.
The fuel may be any fuel suitable for combustion where reduction of NOx is desired. In
one aspect the fuel is a fuel for spark ignition engines such as a gasoline engine.
Preferably the fuel is a fuel for a high compression spontaneous ignition engine. In one
aspect the fuel is selected from diesel, heavy fuel oil, marine gasoil (MGO) and
kerosene. The diesel may be biodiesel, low sulphur diesel and ultra-low sulphur diesel.
Preferably the fuel is marine gasoil. The marine gasoil may be any suitable marine
gasoil. In one aspect it is a fuel having a (i) a density of 0.85-0.89g/cm , a cetane
Number of approximately 45; and a flash point of greater than 55°C.
Aspects of the invention are defined in the appended claims.
The present invention will now be described in further detail in the following examples in
which:
Figures 1, 3a, 3b, 7 to 9 and 13 show graphs; and
Figures 2, 3c, 4, 5, 6, 10, 11, 12 and 14 show images.
EXAMPLES
Example 1
Four polyglycerol esters were prepared and tested. Two were broad range polyglycerol
(BRPG) esters in accordance with the present invention - one based on soya bean oil
and one based on oleic acid. Two were triglycerol esters prepared as a comparison - one
based on soya bean oil and one based on oleic acid.
Manufacture of polyglycerol:
Glycerol: 1250 kg
50% NaOH in water: 9.17 kg
Glycerol and NaOH solution is added to the reactor. Heated to 240°C while taking care
with columns and condensers not to distill off glycerol. The heating to 240°C takes about
3h. Then the pressure is lowered carefully to about 30 mbar to remove reaction water
from the polymerisation of glycerol. After about 7-14 hours at 240°C samples are
50,0
withdrawn from the reactor for measurement of refractive index at 50.0°C, ( ) .
The refractive index is used to determine the termination of the reaction. The refractive
index should be in the interval of 1.4900-1.4920. If the refractive index is not yet in the
interval, the reaction is continued for further 1 hour and another sample is withdrawn for
measurement. This continues until the refractive index is within the interval. When the
polyglycerol is within the stop-interval the temperature is lowered to 120°C.
The glycerol and polyglycerol content of the BRPG samples was determined. The details
of this analysis are given below.
Polyglycerol BRPG BRPG BRPG BRPG
composition Batch 1 Batch 2 Batch 3 Batch 4
(reanalysis in [ ])
%Glycerol 4.81 5.49 4.22 [4.24] 5.15
% CY-Diglycerol 8.68 8.42 9.14 [9.14] 8.13
% Diglycerol 10.04 10.85 8.68 [8.67] 10.58
% CY-Triglycerol 5.94 5.58 6.00 [6.02] 5.70
% Triglycerol 10.57 11.15 9.47 [9.46] 11.00
% CY- 4.20 3.90 3.93 [4.24] 4.06
Tetraglycerol
% Tetraglycerol 8.76 9.12 8.00 [8.00] 9.06
% CY- 4.13 3.60 4.44 [4.38] 3.59
Pentaglycerol
% Pentaglycerol 6.95 7.20 6.44 [6.53] 6.40
% Hexaglycerol 9.36 8.98 8.89 [9.22] 9.58
% Heptaglycerol 8.71 8.15 8.63 [8.96] 9.44
% Octaglycerol 7.27 7.02 8.52 [7.57] 7.02
% Nonaglycerol 5.58 5.20 6.07 [5.80] 5.36
% Decaglycerol 3.31 3.51 4.20 [4.25] 2.76
%Undecaglycerol 1.69 1.82 3.38 [3.54] 2.17
Normalised from 95.89 97.02 95.59 [95.06] 98.53
Specifications of the hydroxyl values and the refractive index for the broad range
polyglycerol of the present invention and the triglycerol used for the esters below are
given below:
Broad range polyglycerol
Hydroxyl value (OHV): 950-990
Refractive index at 50°C: 1.4900-1.4920
Triglycerol
Hydroxyl value (OHV): 1090-1190
Refractive index ( 20°C): 1.4930-1.4970
Manufacture of Triglycerol and Polyglycerol esters:
Polyglycerol PGE 2440/198:
Soyabean oil: 700g
Polyglycerol: 203.2g
50% NaOH in water: 3.80g
The polyglycerol was prepared in accordance with the above process.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Temperature is raised to 90°C. Pressure is lowered to about 50 mBar when the mixture
reaches 90°C. Temperature is then raised to 230°C and held at that temperature for 30
min. Cooled to about 90°C. Pressure equalised with nitrogen at 90°C. The product is
clear.
Analysis: Acid value: 0.3; Saponification value: 146.2; Hydroxyl value: 219.2.
Polyglycerol PGE 2526/160:
Oleic acid 90%: 340g
Polyglycerol: 102g
Glycerol: 37g
50% NaOH in water: 1.75g
The polyglycerol was prepared in accordance with the above process.
All ingredients are charged to a 3-necked flask with mechanical stirring, vigreux column,
condenser, temperature control, nitrogen protection is used, vacuum pump is connected
to the set-up.
Temperature is raised gradually to 235°C. At 208°C reaction water is distilled off. After
80 min. the mixture is clear and the temperature is 235°C. The reaction mixture is
reacted for further 1h.
The pressure is lowered gradually to 75 mBar. Then the mixture reacts for further 1h. A
sample is withdrawn for acid value measurement.
When the acid value is below 2 the product is finished and the temperature is lowered to
90°C. Pressure equalised with nitrogen. The product is clear.
Analysis: Acid value: 0.5; Saponification value: 145.5; Hydroxyl value: 214.9; Alcaline
number: 7.4.
Triglycerol PGE 2528/072 (Comparative):
Soyabean oil: 700g
Triglycerol: 215g
50% NaOH in water: 3.80g
The triglycerol was obtained from Solvay.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Pressure is lowered to about 50 mBar when the mixture reaches 90°C. Temperature is
raised from room temperature to 230°C in 85 min. The reaction mixture is held at 230°C
for 2.5h, then cooled to 90°C and pressure equalised with nitrogen. The product is clear.
Analysis: Acid value: 0.2; Saponification value: 142.6; Iodine value: 95.2; Color 5 1/4,''
Total: 3.0 yellow: 15 red: 1.5.
Triglycerol PGE 2526/159 (Comparative):
Oleic acid 90%: 340g
Triglycerol: 108g
Glycerol: 37g
50% NaOH in water: 1.75g
The triglycerol was obtained from Solvay.
All ingredients are charged to a 3-necked flask with mechanical stirring, vigreux column,
condenser, temperature control, nitrogen protection is used, vacuum pump is connected
to the set-up.
Temperature is raised gradually to 235°C. At 208°C reaction water is observed. After 65
min. the mixture is clear and the temperature is 235°C. The reaction mixture is reacted
for further 1h. The pressure is lowered gradually to 75 mBar, then the mixture reacts for
further 1h. A sample is withdrawn for acid value measurement. When the acid value is
below 2 the product is finished and the temperature is lowered to 90°C. Pressure
equalised with nitrogen. The product is clear.
Analysis: Acid value: 0.8; Saponification value: 143.6; Hydroxyl value: 262.8; Alcaline
number: 4.6.
Four polyglycerol esters based on either soy oil or oleic acid and either triglycerol or
broad range polyglycerol (BRPG) esters were tested in water-in-fuel emulsion (W IF-
emulsion) with 50% water content at 55°C with focus on water droplet size distribution,
stability and emulsion viscosity.
The results of the investigations show that BRPG esters provides smaller water droplets
and reduced water droplet sedimentation during storage compared to triglycerol esters.
Four samples were tested with two polyol distributions (t riglycerol vs. BRPG) and two
fatty acid sources ( soy oil vs. pure oleic acid). The main focus of the test was the effect
of reduced emulsifier addition on the emulsion stability.
EXPERIMENTAL
Four emulsifiers were tested in water-in-fuel emulsions, WIF-emulsions, with 50% water
content at 55°C. The emulsifiers are listed in table 1. Dosages 0.5%, 0.25% and 0.1%
based on the emulsion. The emulsions (200 g) were prepared by slowly adding the water
phase to the fuel (MGO) during homogenization with Ultra Turrex at 20500 rpm for 64 s.
Both the MGO and the water were heated to 55°C prior to emulsification.
The following analyses were carried out immediately after preparation of the emulsion:
1. Water droplet size distribution by NMR.
2. Microscopy by CLSM.
3. Emulsion stability during 3 hours storage at 55°C by imaging and image
analysis.
Polyglycerol Material Fatty acid Polyglycerol
Type composition %
BRPG 2440/198 soy oil 23.8*
BRPG 2526/160 Oleate 27.0
Triglycerol 2528/072 soy oil 23.8*
Triglycerol 2526/159 Oleate 28.6
Table 1 * The low polyol percentage is due to the fatty acid source.
The marine gasoil (diesel) used in the testing was Shell Thermo heating oil.
RESULTS
The water droplet size distribution is shown in Table 2. Note the significant increase in
water droplet size at low emulsifier concentration.
Emulsifier Conc % Conc % Water % Temp D2.5 D50.0
Emulsion Diesel Emulsion °C µ m µ m
2440/198 0.50 1.00 50 55 0.6 7.7
BRPG- soy 0.25 0.50 50 55 3.3 16.6
0.10 0.20 50 55 4.2 63.0
2526/160 0.50 1.00 50 55 0.5 7.1
BRPG - oleate 0.25 0.50 50 55 3.7 18.6
0.10 0.20 50 55 6.7 47.0
2528/072 0.50 1.00 50 55 0.4 6.6
Triglycerol - soy 0.25 0.50 50 55 2.7 17.8
0.10 0.20 50 55 2.8 87.8
2526/159 0.50 1.00 50 55 0.5 7.4
Triglycerol - 0.25 0.50 50 55 1.9 14.9
oleate 0.10 0.20 50 55 4.5 72.7
Table 2 Water droplet size distribution.
The D50.0 values are compared in Figure 1, where the huge increase in droplet size at
0.1% dosage level is clearly seen. The graph also shows that at very stressing conditions
(0.1% emulsifier dosage) PGE based on BRPG (broad range polyglycerol) results in
smaller water droplets than PGE based on triglycerol. At the same time PGE based on
fatty acids from soy oil results in larger droplets than PGE based on pure oleic acid.
The droplet size distribution by CLSM is seen below with a comparison between 0.5%
and 0.1% emulsifier dosage. The huge increase in droplet size at low emulsifier dosage
is clearly seen on the pictures. Pictures of samples with 0.25% emulsifier addition are
shown in Figure 2. Pictures of samples with 0.1%, 0.25% and 0.5% emulsifier addition
are shown in Figure 6.
In Figure 3a, 3b and 3c are shown the degree of water droplet sedimentation in the
emulsions during 3 hours storage at 55°C with 0.5%, 0.25% and 0.1% emulsifier
addition. The degree of sedimentation is expressed as the free diesel oil on top of the
samples in percentage of the total samples height. The values were generated by image
analysis.
The difference in the degree of sedimentation between the dosage levels is to be noted.
At 0.1% dosage the sedimentation is ten-fold larger than at 0.5% dosage level.
The ester of triglycerol and soy oil performs poorly at low concentration. Hence the
performance of this emulsifier is more sensitive to dosage reduction compared to the
broad range polyglycerol ester emulsifiers of the present invention.
At low concentration the two emulsifiers based on BRPG of the present invention
perform better than the emulsifiers based on triglycerol. This is in agreement with the
difference in water droplet size illustrated in Figure 1.
Pictures of the samples are available in Figures 4 and 5 .
CONCLUSION
It is clearly documented that polyglycerol esters based on broad range polyglycerols
results in smaller water droplet and reduced water droplet sedimentation during storage
as compared to polyglycerolesters based on triglycerol. This effect is seen at very low
emulsifier addition (0.1%) representing stressing conditions, which most like a real life
situation. Furthermore it is concluded that a fatty acids composition with high oleic acid
content is superior to a composition with high linoleic acid (soy oil) based on above
attributes.
Example 2
Four further polyglycerol esters were prepared and tested. Each was a broad range
polyglycerol (BRPG) esters in accordance with the present invention and each was
based on rape seed oil. Two were triglycerol esters and two were hexaglycerol esters.
The esters in accordance with the present invention were compared against a
comparison prepared from triglycerol and soy oil (R EF PGE or REF).
EXPERIMENTAL
PGE 2680/060 with polyol 13%:
Rapeseed oil: 920g
Broad Range Hexaglycerol (BRHG): 138g
50% NaOH in water: 1.92g
The hexaglycerol was prepared by polymerisation in the same manner as described in
Example 1.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear.
Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is
held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The
product is clear.
Analysis: Acid value: 0.2; Saponification value: 161.8; Hydroxyl value: 125; Alcaline
number: 3.9
PGE 2680/065 with polyol 10%:
Rapeseed oil: 960g
Broad Range Hexaglycerol (BRHG): 106.6g
50% NaOH in water: 2.4g
The hexaglycerol was prepared by polymerisation in the same manner as described in
Example 1.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear.
Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is
held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The
product is clear.
Analysis: Acid value: 0.2; Saponification value: 168.6; Hydroxyl value: 100.2; Alcaline
number: 4.1
PGE 2680/062 with polyol 23%:
Rapeseed oil: 450g
Broad Range Triglycerol (BRTG): 135g
50% NaOH in water: 0.82g
The triglycerol was prepared by polymerisation in the same manner as described in
Example 1 except the refractive index was at 25 C was changed from 1.4855 to 1.4935.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear.
Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is
held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The
product is clear.
Analysis: Acid value: 0.1; Saponification value: 144.9; Hydroxyl value: 241.4; Alcaline
number: 5.0
PGE 2680/073 with polyol 13%:
Rapeseed oil: 500g
Broad Range Triglycerol ( BRTG): 75g
50% NaOH in water: 0.8g
The triglycerol was prepared by polymerisation in the same manner as described in
Example 1 except the refractive index was at 25 C was changed from 1.4855 to 1.4935.
All ingredients are charged to a 3-necked flask with mechanical stirring, condenser,
temperature control, nitrogen protection is used, vacuum pump is connected to the set-
Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear.
Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is
held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The
product is clear.
Analysis: Acid value: 0.2; Saponification value: 163.9; Hydroxyl value: 147.5; Alcaline
number: 3.7
Polyol Distribution
The polyol distribution of the polyol used in the preparation of each of 2680/062 and
2680/073 was analysed. The analyses was performed twice and an average taken. The
results of this analysis are given in Table 3 below.
Average of 2 Polyol % based on
Analysis 1 Analysis 2 Analyses total Polyols
%Glycerol 11.03
11.08 10.9998
% CY-Diglycerol 6.4
6.42 6.37 7.19%
% Diglycerol 21.54
21.56 21.51 24.20%
% CY-Triglycerol 2.98
2.96 3 3.35%
% Triglycerol 17.8182
17.74 17.89 20.02%
% CY-Tetraglycerol 2.02
1.98 2.06 2.27%
% Tetraglycerol 11.6566
11.52 11.79 13.10%
% CY-Pentaglycerol 2.74
2.78 2.7 3.08%
% Pentaglycerol 6.87
6.8 6.93 7.72%
% Hexaglycerol 6.6
6.53 6.67 7.42%
% Heptaglycerol 4.87
4.84 4.89 5.47%
% Octaglycerol 3.07
3.15 3 3.45%
% Nonaglycerol 1.76
1.9 1.62 1.98%
% Decaglycerol 0.66
0.74 0.58 0.74%
%Undecaglycerol 0
0 0 0.00%
Table 3 - Polyol duplicate analysis
The polyglycerol esters synthesized are summarised in Table 4. Three types of
polyglycerol were included in series, they were two triglycerols and one hexaglycerol The
fatty acid source was either soy oil or rape seed oil.
Sample Polyol Wt. % Polyol Oil
type Type
REF PGE Tri 23.8 Soy
J 2680/053 BRHG 19.0 Soy
J 2680/054 BRHG 16.0 rape seed
J 2680/060 BRHG 13.0 rape seed
J 2680/062 BRTG 23.1 rape seed
J 2680/065 BRHG 10.0 rape seed
J 2680/073 BRTG 13.0 rape seed
Table 4. BRHG / BRTG: Broad range Hexa/Tri-Glycerol
The difference in polyol composition is shown below
The polyol distribution of samples REF PGE, the BRTG used in the preparation of
2680/073 and the BRHG used in the preparation of 2680/060 are shown in Table 5.
REF PGE BRTG BRHG
%Glycerol 5.2
0.1 11
% CY-Diglycerol 9
0 6.4
% Diglycerol 9.7
27 21.5
% CY-Triglycerol 5.7
2.5 3
% Triglycerol 10.3
44.2 17.8
% CY-Tetraglycerol 4
4.1 2
% Tetraglycerol 8.5
12.4 11.7
% CY-Pentaglycerol 4.1
1.6 2.7
% Pentaglycerol 6.8
4.2 6.9
% Hexaglycerol 9.2
2.5 6.6
% Heptaglycerol 8.5
1.2 4.9
% Octaglycerol 7
0 3.1
% Nonaglycerol 5.4
0 1.8
% Decaglycerol 3.6
0 0.7
%Undecaglycerol 3.1
Table 5. polyol distribution of samples
The viscosity of each emulsifier was measured on a Physica Rheometer using the
following setup:
Temp: 60°C to -10°C (1 °C/min), Shear rate : 23 1/s, Measuring system: DG26.7 7-
SN711; d=0mm
Selected emulsifiers (REF PGE, J2680/060, J2680/065, J2680/073) were further tested
in WIF-emulsions with 50% water content at 55°C at 0.1% and 0.2% dosage. Diesel
quality: MGO.
WIF-samples were prepared as described in Example 1.
RESULTS
The droplet size distribution is shown in Table 6 and graphically in Figure 9 for D50.0
values. Samples 2680/065 and 2680/073 were not stable enough to allow NMR
measurement.
Sample Dosage D2.5 D50.0 comments
m m
REF PGE 0.1 1.6 81.0
J 2680/060 0.1 5.3 100.0
J 2680/065 0.1 - - Too fast
sedimentation
J 2680/073 0.1 - - Water phase
separation
REF PGE 0.2 4.2 19.3
J 2680/060 0.2 7.9 32.6
J 2680/065 0.2 3.7 100.0
J 2680/073 0.2 - - Water phase
separation
Table 6 water droplet size distribution
The CLSM pictures of the emulsion are shown in Figure 10. The images were recorded
immediately after emulsification. Samples 2680/065 and 2680/073 both provides much
bigger water droplets at both emulsifier dosage levels as compared to the reference
( REF PGE) and 2680/060. .
The CLSM images of Figure 11 show a dramatic increase in the water droplet size at low
emulsifier dosage for samples 2680/065 and 2680/073 as a sign of reduced functionality.
Also at 0.2% dosage level, the droplets are clearly larger than for samples REF PGE and
2680/060.
Sedimentation and water phase separation after 1h, 2, and 3h storage at 55°C for
sample 2680/073 are shown in Figure 12. Such pronounced water separation is unusual
with WIF-emulsions. Sedimentation at rest however is not a problem as a homogeneous
emulsion will be reformed during flow
Images of the emulsions are shown in Figure 14.
The degree of water droplet sedimentation in the emulsions expressed as the amount of
free oil on top formed during 3 hours of storage at 55°C is shown in Figure 13.
All publications mentioned in the above specification are herein incorporated by
reference. Various modifications and variations of the described methods and system of
the invention will be apparent to those skilled in the art without departing from the scope
and spirit of the invention. Although the invention has been described in connection with
specific preferred embodiments, it should be understood that the invention as claimed
should not be unduly limited to such specific embodiments. Indeed, various modifications
of the described modes for carrying out the invention which are obvious to those skilled
in chemistry or related fields are intended to be within the scope of the following claims.
Where the terms “comprise”, “comprises”, “comprised” or “comprising” are used in this
specification , they are to be interpreted as specifying the presence of the stated
features, integers, steps or components referred to, but not to preclude the presence or
addition of one or more other feature, integer, step, component or group thereof.
Further, any prior art reference or statement provided in the specification is not to be
taken as an admission that such art constitutes, or is to be understood as constituting,
part of the common general knowledge.
Claims (37)
1. A fuel composition comprising: (a) a fuel; and 5 (b) a polyglycerol ester of a fatty acid, wherein the polyglycerol ester of a fatty acid is present in an amount of no greater than 0.5 weight% based on the total fuel composition; wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of 10 the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; 15 pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined 20 weight of the polyglycerols; octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined weight of the polyglycerols; 25 decaglycerol in an amount of 0.0 to 8.0 weight% based on the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of the polyglycerols. 30
2. The fuel composition according to Claim 1, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 28.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of 35 the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; 5 hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; octaglycerol in an amount of 4.0 to 12.0 weight% based on the combined weight 10 of the polyglycerols; nonaglycerol in an amount of 2.0 to 10.0 weight% based on the combined weight of the polyglycerols; decaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols; and 15 unadecaglycerol in an amount of 0.1 to 7.0 weight% based on the combined weight of the polyglycerols.
3. The fuel composition according to Claim 1, wherein the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 25.0 weight% 20 based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 21.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols; 25 the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.5 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in 30 an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
4. The fuel composition according to Claim 2, wherein the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 35 5.0 to 13.0 weight% based on the combined weight of the polyglycerols the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols; the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0 to 13.0 5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 1.0 to 8.0 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
5. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of the polyglycerol composition used to form the polyglycerol ester of a fatty acid 15 comprises diglycerol in an amount of 15.0 to 23.5 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 13.5 to 20.5 weight% based on the combined weight of the polyglycerols; 20 the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 10.0 to 17.0 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in an amount of 8.0 to 14.5 weight% based on the combined 25 weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 8.0 to 11.5 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid 30 comprises heptaglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 6.5 to 10.0 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 4.0 to 8.0 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid 5 comprises decaglycerol in an amount of 1.5 to 6.0 weight% based on the combined weight of the polyglycerols; and the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 0.5 to 5.0 weight% based on the combined weight of the polyglycerols.
6. The fuel composition according to Claim 5, wherein the diglycerol comprises acyclic diglycerol in an amount of 8.0 to 12.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols; 15 the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 4.5 to 7.5 weight% based on the combined weight of the polyglycerols; the tetraglycerol comprises acyclic tetraglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in 20 an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 5.0 to 9.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols. 25
7. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises diglycerol in an amount of 17.6 to 21.0 weight% based on the combined 30 weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 15.9 to 18.1 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 12.5 to 14.0 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid 5 comprises pentaglycerol in an amount of 10.5 to 12.2 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 9.3 to 10.1 weight% based on the combined weight of the polyglycerols; 10 the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in an amount of 8.6 to 9.9 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 7.3 to 8.9 weight% based on the combined 15 weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 5.5 to 6.4 weight% based on the combined weight of the polyglycerols; the polyglycerol composition used to form the polyglycerol ester of a fatty acid 20 comprises decaglycerol in an amount of 2.9 to 4.5 weight% based on the combined weight of the polyglycerols; and the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 1.8 to 3.7 weight% based on the combined weight of the polyglycerols.
8. The fuel composition according to Claim 7, wherein the diglycerol comprises acyclic diglycerol in an amount of 9.1 to 11.4 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 8.5 to 9.5 weight% based on the combined weight of the polyglycerols; 30 the triglycerol comprises acyclic triglycerol in an amount of 10.0 to 11.8 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 5.9 to 6.3 weight% based on the combined weight of the polyglycerols; the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.4 to 9.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in 35 an amount of 4.1 to 4.4 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.7 to 7.6 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 3.8 to 4.6 weight% based on the combined weight of the polyglycerols. 5
9. The fuel composition according to Claim 1, wherein in the polyglycerol composition used to form the polyglycerol ester of a fatty acid the diglycerol comprises acyclic diglycerol in an amount of 9.0 to 24.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 10.0 weight% based on the combined weight of the polyglycerols; 10 the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 20.5 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 3.5 to 6.5 weight% based on the combined weight of the polyglycerols; the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.0 to 13.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in 15 an amount of 2.0 to 4.5 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.0 to 9.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.0 to 5.0 weight% based on the combined weight of the polyglycerols. 20
10. The fuel composition according to Claim 7, wherein in the polyglycerol composition used to form the polyglycerol ester of a fatty acid the diglycerol comprises acyclic diglycerol in an amount of 20.0 to 26.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 8.0 weight% based on the combined weight of the polyglycerols; 25 the triglycerol comprises acyclic triglycerol in an amount of 18.0 to 21.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 5.0 weight% based on the combined weight of the polyglycerols; the tetraglycerol comprises acyclic tetraglycerol in an amount of 11.0 to 14.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in 30 an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols; and the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.5 to 9.5 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols.
11. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 880 to 1230 mg KOH/g. 5
12. The fuel composition according to Claims 11, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1130 to 1230 mg KOH/g.
13. The fuel composition according to Claim 11, wherein the polyglycerol composition 10 used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 880 to 1060 mg KOH/g.
14. The fuel composition according to Claim 11, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 950 to 990 15 mg KOH/g.
15. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 25 C of from 1.4855 to 1.4935.
16. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50 C of from 1.4895 to 1.4925. 25
17. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50 C of from 1.4900 to 1.4920.
18. The fuel composition according to any one of the preceding Claims, wherein the 30 polyglycerol ester of a fatty acid has a viscosity of less than 700 mPa s at 20°C
19. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol ester of a fatty acid has a viscosity of less than 200 mPa s at 20°C
20. The fuel composition according to any one of the preceding Claims, wherein the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and a fatty acid triglyceride in a ratio of polyglycerol to fatty acid triglyceride of from 1:1 to 1:8. 5
21. The fuel composition according to any one of the preceding Claims, wherein the (b) a polyglycerol ester of a fatty acid is present in an amount of no greater than 0.25 weight% based on the total fuel composition.
22. The fuel composition according to any one of the preceding Claims, wherein the 10 (b) a polyglycerol ester of a fatty acid is present in an amount of no greater than 0.2 weight% based on the total fuel composition.
23. The fuel composition according to any one of the preceding Claims, wherein the (b) a polyglycerol ester of a fatty acid is present in an amount of no greater than 0.1 15 weight% based on the total fuel composition.
24. The fuel composition according to any one of the preceding Claims, wherein the fuel is selected from diesel, heavy fuel oil, marine gasoil and kerosene. 20
25. The fuel composition according to Claim 24, wherein the fuel is marine gasoil.
26. The fuel composition according to any one of the preceding Claims, wherein the fuel composition further comprises (c) water. 25
27. The fuel composition according to Claim 26, wherein the fuel composition further comprises ( c) water in an amount of from 10 to 70 wt.% based on the total fuel composition.
28. The fuel composition according to Claim 26, wherein the fuel composition further 30 comprises (c) water in an amount of from 30 to 60 wt.% based on the total fuel composition.
29. The fuel composition according to Claim 26, wherein the fuel composition further comprises (c) water in an amount of from 33 to 50 wt.% based on the total fuel 35 composition.
30. A method for improving the stability of a fuel composition containing (a) fuel and (c) water, the method comprising mixing with the fuel and water, (b) a polyglycerol ester of a fatty acid, wherein the polyglycerol ester of a fatty acid is 5 present in an amount of no greater than 0.5 weight% based on the total fuel composition; wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; 10 triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined 15 weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; 20 octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on the combined weight 25 of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of the polyglycerols.
31. The method according to Claim 30, characterised by the features of any one of 30 Claims 2 to 29.
32. Use of a polyglycerol ester of a fatty acid for improving the stability of a fuel composition containing fuel and water; wherein the polyglycerol ester of a fatty acid is present in an amount of no greater than 35 0.5 weight% based on the total fuel composition; and wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; 5 triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined 10 weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; 15 octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined weight of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on the combined weight 20 of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of the polyglycerols.
33. A kit for preparing a fuel composition as defined in any one of Claims 1 to 29, the 25 kit comprising a polyglycerol ester of a fatty acid wherein the polyglycerol ester of a fatty acid is present in an amount of no greater than 0.5 weight% based on the total fuel composition; and wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of 30 diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight 35 of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; 5 heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols; nonaglycerol in an amount of 1.5 to 10.0 weight% based on the combined weight 10 of the polyglycerols; decaglycerol in an amount of 0.0 to 8.0 weight% based on the combined weight of the polyglycerols; and unadecaglycerol in an amount of 0.0 to 7.0 weight% based on the combined weight of the polyglycerols. 15 together with instructions for use to prepare the fuel composition.
34. The fuel composition according to any one of Claims 1 to 29, substantially as hereinbefore described with reference to any one of the Examples. 20
35. The method according to any one of Claims 30 or 31, substantially as hereinbefore described with reference to any one of the Examples.
36. The use according to Claim 32, substantially as hereinbefore described with reference to any one of the Examples.
37. The kit according to Claim 33, substantially as hereinbefore described with reference to any one of the Examples.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB1111029.3A GB201111029D0 (en) | 2011-06-29 | 2011-06-29 | Composition |
GB1111029.3 | 2011-06-29 | ||
PCT/EP2012/062713 WO2013001064A1 (en) | 2011-06-29 | 2012-06-29 | Composition |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ618376A true NZ618376A (en) | 2015-08-28 |
NZ618376B2 NZ618376B2 (en) | 2015-12-01 |
Family
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GB201111029D0 (en) | 2011-08-10 |
RU2014102771A (en) | 2015-08-10 |
PL2726579T3 (en) | 2020-01-31 |
US20140318004A1 (en) | 2014-10-30 |
CA2839237A1 (en) | 2013-01-03 |
DK2726579T3 (en) | 2019-10-28 |
BR112013033666A2 (en) | 2017-01-24 |
MX2013014365A (en) | 2014-01-31 |
CN103619999A (en) | 2014-03-05 |
JP2014518303A (en) | 2014-07-28 |
SG195249A1 (en) | 2013-12-30 |
EP2726579A1 (en) | 2014-05-07 |
WO2013001064A1 (en) | 2013-01-03 |
CN103619999B (en) | 2015-10-14 |
ZA201309110B (en) | 2015-03-25 |
MA35176B1 (en) | 2014-06-02 |
AU2012277783A1 (en) | 2013-12-19 |
LT2726579T (en) | 2019-10-10 |
KR20140061366A (en) | 2014-05-21 |
EP2726579B1 (en) | 2019-07-24 |
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