U.S. patent application number 14/129652 was filed with the patent office on 2014-10-30 for composition.
The applicant listed for this patent is Allan Torben Bech, Maja Duelund, Jens Mogens Nielsen. Invention is credited to Allan Torben Bech, Maja Duelund, Jens Mogens Nielsen.
Application Number | 20140318004 14/129652 |
Document ID | / |
Family ID | 44485343 |
Filed Date | 2014-10-30 |
United States Patent
Application |
20140318004 |
Kind Code |
A1 |
Nielsen; Jens Mogens ; et
al. |
October 30, 2014 |
COMPOSITION
Abstract
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.
Inventors: |
Nielsen; Jens Mogens;
(Galten, DK) ; Duelund; Maja; (Odder, DK) ;
Bech; Allan Torben; (Brabrand, DK) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Nielsen; Jens Mogens
Duelund; Maja
Bech; Allan Torben |
Galten
Odder
Brabrand |
|
DK
DK
DK |
|
|
Family ID: |
44485343 |
Appl. No.: |
14/129652 |
Filed: |
June 29, 2012 |
PCT Filed: |
June 29, 2012 |
PCT NO: |
PCT/EP2012/062713 |
371 Date: |
July 1, 2014 |
Current U.S.
Class: |
44/389 |
Current CPC
Class: |
C10L 1/328 20130101;
C10L 2250/084 20130101; C10L 2230/14 20130101; C10L 1/19 20130101;
C10L 1/191 20130101 |
Class at
Publication: |
44/389 |
International
Class: |
C10L 1/19 20060101
C10L001/19 |
Foreign Application Data
Date |
Code |
Application Number |
Jun 29, 2011 |
GB |
1111029.3 |
Claims
1. 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.
2. A 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 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 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.
3. A fuel composition according to claim 1 wherein 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; 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.
4. A 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 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 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. A fuel composition according to claim 1 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 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.
6. A 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; 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.
7. A fuel composition according to claim 1 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 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.
8. A 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; 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.
9. A 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; 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.
10. A 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; 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.
11. A fuel composition according to claim 1 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.
12. A 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 1130 to 1230 mg KOH/g.
13. A 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 880 to 1060 mg KOH/g.
14. A 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. A fuel composition according to claim 1 wherein the
polyglycerol composition used to form the polyglycerol ester of a
fatty acid has a refractive index at 25.degree. C. of from 1.4855
to 1.4935.
16. A fuel composition according to claim 1 wherein the
polyglycerol composition used to form the polyglycerol ester of a
fatty acid has a refractive index at 50.degree. C. of from 1.4895
to 1.4925.
17. A fuel composition according to claim 1 wherein the
polyglycerol composition used to form the polyglycerol ester of a
fatty acid has a refractive index at 50.degree. C. of from 1.4900
to 1.4920.
18. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid has a viscosity of less than 700
mPa s at 20.degree. C.
19. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid has a viscosity of less than 200
mPa s at 20.degree. C.
20. A fuel composition according to claim 1 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.
21. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid is present in an amount of no
greater than 0.5 wt % based on the total fuel composition.
22. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid is present in an amount of no
greater than 0.25 wt % based on the total fuel composition.
23. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid is present in an amount of no
greater than 0.2 wt % based on the total fuel composition.
24. A fuel composition according to claim 1 wherein the
polyglycerol ester of a fatty acid is present in an amount of no
greater than 0.1 wt % based on the total fuel composition.
25. A fuel composition according to claim 1 wherein the fuel is
selected from diesel, heavy fuel oil, marine gasoil and
kerosene.
26. A fuel composition according to claim 25 wherein the fuel is
marine gasoil.
27. A fuel composition according to claim 1, wherein the fuel
composition further comprises water.
28. A fuel composition according to claim 27, wherein the fuel
composition further comprises water in an amount of from 10 to 70
wt. % based on the total fuel composition.
29. A fuel composition according to claim 27, wherein the fuel
composition further comprises water in an amount of from 30 to 60
wt. % based on the total fuel composition.
30. A fuel composition according to claim 27, wherein the fuel
composition further comprises water in an amount of from 33 to 50
wt. % based on the total fuel composition.
31. A method for improving the stability of a fuel composition
containing fuel and water, the method comprising mixing with the
fuel and water, 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.
32. (canceled)
33. (canceled)
34. A kit for preparing a fuel composition, the kit comprising 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; unadecaglycerol in an amount
of 0.0 to 7.0 weight % based on the combined weight of the
polyglycerols; and instructions to prepare the fuel
composition.
35. (canceled)
36. (canceled)
37. (canceled)
38. (canceled)
Description
[0001] The present invention relates to a composition. In
particular the present invention relates to fuel compositions
having reduced nitrogen oxide emissions when combusted.
[0002] As discussed in U.S. Pat. No. 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.
[0003] 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.
[0004] 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.
[0005] 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.
[0006] 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.
[0007] 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.
[0008] The present invention alleviates the problems of the prior
art.
[0009] In one aspect the present invention provides a fuel
composition comprising:
[0010] (a) a fuel; and
[0011] (b) a polyglycerol ester of a fatty acid;
[0012] wherein the polyglycerol composition used to form the
polyglycerol ester of a fatty acid comprises a mixture of
[0013] 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.
[0014] 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;
[0015] wherein the polyglycerol composition used to form the
polyglycerol ester of a fatty acid comprises a mixture of
[0016] 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.
[0017] 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.
[0018] 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;
[0019] wherein the polyglycerol composition used to form the
polyglycerol ester of a fatty acid comprises a mixture of
[0020] 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.
[0021] 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.
[0022] 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.
[0023] Composition
[0024] As previously mentioned, in one aspect the present nvention
provides a fuel composition comprising:
[0025] (a) a fuel; and
[0026] (b) a polyglycerol ester of a fatty acid;
[0027] wherein the polyglycerol composition used to form the
polyglycerol ester of a fatty acid comprises a mixture of
[0028] 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.
[0029] Polyglycerol Ester of a Fatty Acid
[0030] 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.
[0031] 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.
[0032] 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.
[0033] As discussed here in the polyglycerol composition used to
form the polyglycerol ester of to 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.
[0034] 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.
[0035] In one preferred aspect [0036] 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; [0037] 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; [0038] 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 [0039] 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.
[0040] 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 5.0 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 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. 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.
[0041] 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 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. 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.
[0042] In one preferred aspect [0043] 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 [0044] 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; [0045] 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 [0046] 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.
[0047] In one preferred aspect [0048] 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 [0049] 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;
[0050] 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
[0051] 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.
[0052] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0053] 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 [0054] 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;
[0055] 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 [0056] 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. [0057] hexaglycerol in an amount of 6.0 to 13.5
weight % based on the combined weight of the polyglycerols [0058]
heptaglycerol in an amount of 5.0 to 13.0 eight % based on the
combined weight of the polyglycerols [0059] octaglycerol in an
amount of 4.0 to 12.0 weight % based on the combined weight of the
polyglycerols [0060] nonaglycerol in an amount of 2.0 to 10.0
weight % based on the combined weight of the polyglycerols [0061]
decaglycerol in an amount of 0.5 to 8.0 weight % based on the
combined weight of the polyglycerols; and [0062] unadecaglycerol in
an amount of 0.1 to 7.0 weight % based on the combined weight of
the polyglycerols.
[0063] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0064] 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 [0065] 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;
[0066] 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 [0067] 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.
[0068] hexaglycerol in an amount of 6.0 to 13.5 weight % based on
the combined weight of the polyglycerols [0069] heptaglycerol in an
amount of 5.0 to 13.0 weight % based on the combined weight of the
polyglycerols [0070] octaglycerol in an amount of 4.0 to 12.0
weight % based on the combined weight of the polyglycerols [0071]
nonaglycerol in an amount of 2.0 to 10.0 weight % based on the
combined weight of the polyglycerols [0072] decaglycerol in an
amount of 0.5 to 8.0 weight % based on the combined weight of the
polyglycerols; and [0073] unadecaglycerol in an amount of 0.1 to
7.0 weight % based on the combined weight of the polyglycerols.
[0074] 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.
[0075] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0076] 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;
[0077] 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;
[0078] 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;
[0079] 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;
[0080] 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;
[0081] 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;
[0082] 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;
[0083] 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;
[0084] 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
[0085] 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.
[0086] 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.
[0087] In one preferred aspect [0088] 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;
[0089] 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;
[0090] 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
[0091] 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.
[0092] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0093] 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; [0094] 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;
[0095] 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 [0096] 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 25 to 6.0 weight % based on the combined weight of the
polyglycerols. [0097] 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; [0098] 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; [0099] 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; [0100] 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; [0101] 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 [0102] 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.
[0103] 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.
[0104] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0105] 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;
[0106] 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;
[0107] 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;
[0108] 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;
[0109] 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;
[0110] 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;
[0111] 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;
[0112] 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;
[0113] 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
[0114] 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.
[0115] 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.
[0116] In one preferred aspect [0117] 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; [0118] 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; [0119] 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 [0120] 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.
[0121] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0122] 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; [0123] 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;
[0124] 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 [0125] 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. [0126] 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; [0127] 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; [0128] 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; [0129] 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; [0130] 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 [0131] 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.
[0132] 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.
[0133] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0134] diglycerol in an amount of 18.0 to 32.0 weight % based on
the combined weight of the polyglycerols; [0135] triglycerol in an
amount of 16.0 to 24.0 weight % based on the combined weight of the
polyglycerols, [0136] tetraglycerol in an amount of 12.0 to 16.0
weight % based on the combined weight of the polyglycerols; [0137]
pentaglycerol in an amount of 8.0 to 12.0 weight % based on the
combined weight of the polyglycerols; [0138] hexaglycerol in an
amount of 7.0 to 11.0 weigh based on the combined weight of the
polyglycerols; [0139] heptaglycerol in an amount of 5.0 to 10.0
weight % based on the combined weight of the polyglycerols; [0140]
octaglycerol in an amount of 3.0 to 9.0 weight % based on the
combined weight of the polyglycerols; [0141] nonaglycerol in an
amount of 1.5 to 7.0 weight % based on the combined weight of the
polyglycerols; [0142] decaglycerol in an amount of 0.0 to 4.5
weight % based on the combined weight of the polyglycerols; and
[0143] unadecaglycerol in an amount of 0.0 to 4.0 weight % based on
the combined weight of the polyglycerols.
[0144] 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 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. 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.
[0145] In one preferred aspect in the polyglycerol composition used
to form the polyglycerol ester of a fatty acid [0146] 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; [0147] 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; [0148] 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 [0149] 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.
[0150] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0151] to 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; [0152] 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;
[0153] 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; [0154] 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;
[0155] hexaglycerol in an amount of 7.0 to 11.0 weight % based on
the combined weight of the polyglycerols; [0156] heptaglycerol in
an amount of 5.0 to 10.0 weight % based on the combined weight of
the polyglycerols; [0157] octaglycerol in an amount of 3.0 to 9.0
weight % based on the combined weight of the polyglycerols; [0158]
nonaglycerol in an amount of 1.5 to 7.0 weight % based on the
combined weight of the polyglycerols; [0159] decaglycerol in an
amount of 0.0 to 4.5 weight % based on the combined weight of the
polyglycerols; and [0160] unadecaglycerol in an amount of 0.0 to
4.0 weight % based on the combined weight of the polyglycerols.
[0161] 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.
[0162] 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.
[0163] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0164] diglycerol in an amount of 26.0 to 34.0 weight % based on
the combined weight of the polyglycerols; [0165] triglycerol in an
amount of 21.0 to 25.0 weight % based on the combined weight of the
polyglycerols; [0166] tetraglycerol in an amount of 12.0 to 17.0
weight % based on the combined weight of the polyglycerols; [0167]
pentaglycerol in an amount of 8.0 to 12.0 weight % based on the
combined weight of the polyglycerols; [0168] hexaglycerol in an
amount of 6.0 to 10.0 weight % based on the combined weight of the
polyglycerols; [0169] heptaglycerol in an amount of 4.5 to 7.5
weight % based on the combined weight of the polyglycerols; [0170]
octaglycerol in an amount of 2.5 to 5.5 weight % based on the
combined weight of the polyglycerols; [0171] nonaglycerol in an
amount of 1.0 to 3.0 weight % based on the combined weight of the
polyglycerols; [0172] decaglycerol in an amount of 0.0 to 1.0
weight % based on the combined weight of the polyglycerols; and
[0173] unadecaglycerol in an amount of 0.0 to 0.5 weight % based on
the combined weight of the polyglycerols.
[0174] 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.
[0175] 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;
[0176] In one preferred aspect in the polyglycerol composition used
to form the polyglycerol ester of a fatty acid [0177] 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; [0178] 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; [0179] 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 [0180] 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.
[0181] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid comprises a mixture of
[0182] 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; [0183] 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;
[0184] 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; [0185] 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;
[0186] hexaglycerol in an amount of 6.0 to 10.0 weight % based on
the combined weight of the polyglycerols: [0187] heptaglycerol in
an amount of 4.5 to 7.5 weight % based on the combined weight of
the polyglycerols: [0188] octaglycerol in an amount of 2.5 to 5.5
weight % based on the combined weight of the polyglycerols; [0189]
nonaglycerol in an amount of 1.0 to 3.0 weight % based on the
combined weight of the polyglycerols; [0190] decaglycerol in an
amount of 0.0 to 1.0 weight % based on the combined weight of the
polyglycerols; and [0191] unadecaglycerol in an amount of 0.0 to
0.5 weight % based on the combined weight of the polyglycerols.
[0192] 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.
[0193] 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.
[0194] A highly preferred fatty acid of the polyglycerol ester of a
fatty acid is oleic acid ((9Z)-Octadec-9-enoic acid).
[0195] 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.
[0196] 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.
[0197] In one preferred aspect the polyglycerol composition used to
form the polyglycerol ester of a fatty acid has a refractive index
at 50.degree. 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.degree. 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.degree. 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 is refractive index at
50.degree. 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.degree. C. of from 1.4855
to 1.4935.
[0198] In one preferred aspect the polyglycerol ester of a fatty
acid has a viscosity of less than 700 mPa s at 20.degree. C., such
as less than 600 mPa s at 20.degree. C., such as less than 500 mPa
s at 20.degree. C., such as less than 400 mPa s at 20.degree. C.,
such as less than 350 mPa s at 20.degree. C., such as less than 300
mPa s at 20.degree. C., such as less than 250 mPa s at 20.degree.
C., such as less than 200 mPa s at 20.degree. 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.degree. C., is an
important factor in the preparation of an effective emulsion.
[0199] 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 FIG. 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 1:67.
[0200] Fuel Composition
[0201] 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.
[0202] 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.
[0203] Fuel
[0204] 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.
[0205] 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.
[0206] 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.
[0207] 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 0.85-0.89
g/cm.sup.3, a cetane Number of approximately 45; and a flash point
of greater than 55.degree. C.
[0208] Aspects of the invention are defined in the appended
claims.
[0209] The present invention will now be described in further
detail in the following examples in which:
[0210] FIGS. 1, 3a, 3b, 7 to 9 and 13 show graphs; and
[0211] FIGS. 2, 3c, 4, 5, 6, 10, 11, 12 and 14 show images.
EXAMPLES
Example 1
[0212] 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.
[0213] Manufacture of polyglycerol;
[0214] Glycerol: 1250 kg
[0215] 50% NaOH in water: 9.17 kg
[0216] Glycerol and NaOH solution is added to the reactor. Heated
to 240.degree. C. while taking care with columns and condensers not
to distill off glycerol. The heating to 240.degree. C. takes about
3 h. 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.degree. C. samples are withdrawn from the
reactor for measurement of refractive index at 50.0.degree. C.,
(n.sub.D.sup.50.0).
[0217] 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.degree. C.
[0218] The glycerol and polyglycerol content of the BRPG samples
was determined. The details of this analysis are given below.
TABLE-US-00001 BRPG Polyglycerol BRPG BRPG Batch 3 BRPG composition
Batch 1 Batch 2 (reanalysis in [ ]) Batch 4 % 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
[0219] 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:
[0220] Broad Range Polyglycerol
[0221] Hydroxyl value (OHV): 950-990
[0222] Refractive index at 50.degree. C.: 1.4900-1.4920
[0223] Triglycerol
[0224] Hydroxyl value (OHV): 1090-1190
[0225] Refractive index (20.degree. C.): 1.4930-1.4970
[0226] Manufacture of Triglycerol and Polyglycerol Esters:
[0227] Polyglycerol PGE 2440/198:
[0228] Soyabean oil: 700 g
[0229] Polyglycerol: 203.2 g
[0230] 50% NaOH in water: 3.80 g
[0231] The polyglycerol was prepared in accordance with the above
process.
[0232] 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-up.
[0233] Temperature is raised to 90.degree. C. Pressure is lowered
to about 50 mBar when the mixture reaches 90.degree. C. Temperature
is then raised to 230.degree. C. and held at that temperature for
30 min, Cooled to about 90.degree. C. Pressure equalised with
nitrogen at 90.degree. C. The product is clear.
[0234] Analysis: Acid value: 0.3; Saponification value: 146.2;
Hydroxyl value: 219.2,
[0235] Polyglycerol PGE 2526/160:
[0236] Oleic acid 90%: 340 g
[0237] Polyglycerol: 102 g
[0238] Glycerol: 37 g
[0239] 50% NaOH in water: 1.75 g
[0240] The polyglycerol was prepared in accordance with the above
process.
[0241] 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.
[0242] Temperature is raised gradually to 235.degree. C. At
208.degree. C. reaction water is distilled off. After 80 min. the
mixture is clear and the temperature is 235.degree. C. The reaction
mixture is reacted for further 1 h.
[0243] The pressure is lowered gradually to 75 mBar. Then the
mixture reacts for further 1 h. A sample is withdrawn for acid
value measurement.
[0244] When the acid value is below 2 the product is finished and
the temperature is lowered to 90.degree. C. Pressure equalised with
nitrogen. The product is clear.
[0245] Analysis: Acid value: 0.5; Saponification value: 145.5;
Hydroxyl value: 214.9; Alcaline number: 7.4.
[0246] Triglycerol PGE 2528/072 (Comparative):
[0247] Soyabean oil: 700 g
[0248] Triglycerol: 215 g
[0249] 50% NaOH in water: 3.80 g
[0250] The triglycerol was obtained from Solvay.
[0251] 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-up.
[0252] Pressure is lowered to about 50 mBar when the mixture
reaches 90.degree. C. Temperature is raised from room temperature
to 230.degree. C. in 85 min. The reaction mixture is held at
230.degree. C. for 2.5 h, then cooled to 90.degree. C. and pressure
equalised with nitrogen. The product is clear.
[0253] Analysis: Acid value: 0.2; Saponification value: 142.6;
Iodine value: 95.2; Color 51/4'', Total: 3.0 yellow: 15 red:
1.5.
[0254] Triglycerol PGE 2526/159 (Comparative):
[0255] Oleic acid 90%: 340 g
[0256] Triglycerol: 108 g
[0257] Glycerol: 37 g
[0258] 50% NaOH in water: 1.75 g
[0259] The triglycerol was obtained from Solvay.
[0260] 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.
[0261] Temperature is raised gradually to 235.degree. C. At
208.degree. C. reaction water is observed. After 65 min. the
mixture is clear and the temperature is 235.degree. C. The reaction
mixture is reacted for further 1 h. The pressure is lowered
gradually to 75 mBar, then the mixture reacts for further 1 h. 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.degree. C. Pressure equalised with nitrogen. The product is
clear.
[0262] Analysis: Acid value: M: Saponification value: 143.6;
Hydroxyl value: 262.8; Alcaline number: 4.6,
[0263] 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 (WIF-emulsion) with
50% water content at 55.degree. C. with focus on water droplet size
distribution, stability and emulsion viscosity.
[0264] The results of the investigations show that BRPG esters
provides smaller water droplets and reduced water droplet
sedimentation during storage compared to triglycerol esters.
[0265] Four samples were tested with two polyol distributions
(triglycerol 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
[0266] Four emulsifiers were tested in water-in-fuel emulsions,
WIF-emulsions, with 50% water content at 55.degree. 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.degree. C. prior to
emulsification. The following analyses were carried out immediately
after preparation of the emulsion: [0267] 1. Water droplet size
distribution by NMR. [0268] 2. Microscopy by CLSM. [0269] 3.
Emulsion stability during 3 hours storage at 55.degree. C. by
imaging and image analysis.
TABLE-US-00002 [0269] TABLE 1 Polyglycerol Fatty acid Polyglycerol
Type Material 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 *The low polyol percentage is due to the fatty
acid source.
[0270] The marine gasoil (diesel) used in the testing was Shell
Thermo heating oil.
Results
[0271] The water droplet size distribution is shown in Table 2.
Note the significant increase in water droplet size at low
emulsifier concentration.
TABLE-US-00003 TABLE 2 Water droplet size distribution. Conc % Conc
% Water % Temp D2.5 D50.0 Emulsifier Emulsion Diesel Emulsion
.degree. C. .mu.m .mu.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 - 0.25
0.50 50 55 2.7 17.8 soy 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
[0272] The D50.0 values are compared in FIG. 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.
[0273] 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 FIG. 2. Pictures of samples with 0.1%, 0.25% and 0.5%
emulsifier addition are shown in FIG. 6.
[0274] In FIGS. 3a, 3b and 3c are shown the degree of water droplet
sedimentation in the emulsions during 3 hours storage at 55.degree.
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.
[0275] 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.
[0276] 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.
[0277] 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 FIG. 1.
[0278] Pictures of the samples are available in FIGS. 4 and 5.
Conclusion
[0279] 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
[0280] 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.
[0281] The esters in accordance with the present invention were
compared against a comparison prepared from triglycerol and soy oil
(REF PGE or REF).
Experimental
[0282] PGE 2680/060 with polyol 13%:
[0283] Rapeseed oil: 920 g
[0284] Broad Range Hexaglycerol (BRHG): 138 g
[0285] 50% NaOH in water: 1.92 g
[0286] The hexaglycerol was prepared by polymerisation in the same
manner as described in Example 1.
[0287] 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-up.
[0288] Pressure is lowered to 50-100 mBar when the mixture reaches
235.degree. C. and is clear. Temperature is raised from room
temperature to 235.degree. C. in 50 min. The reaction mixture is
held at 235.degree. C. for 2.5 h, then cooled to 100.degree. C. and
pressure equalised with nitrogen. The product is clear.
[0289] Analysis: Acid value: 0.2; Saponification value: 161.8;
Hydroxyl value: 125; Alcaline number: 3.9
[0290] PGE 2680/065 with polyol 10%;
[0291] Rapeseed oil: 960 g
[0292] Broad Range Hexaglycerol (BRHG): 106.6 g
[0293] 50% NaOH in water: 2.4 g
[0294] The hexaglycerol was prepared by polymerisation in the same
manner as described in Example 1.
[0295] 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-up.
[0296] Pressure is lowered to 50-100 mBar when the mixture reaches
235.degree. C. and is clear. Temperature is raised from room
temperature to 235.degree. C. in 50 min. The reaction mixture is
held at 235.degree. C. for 2.5 h; then cooled to 100.degree. C. and
pressure equalised with nitrogen. The product is clear.
[0297] Analysis: Acid value: 0.2: Saponification value: 168.6;
Hydroxyl value: 100.2; Alcaline number: 4.1
[0298] PGE 2680/062 with polyol 23%:
[0299] Rapeseed oil: 450 g
[0300] Broad Range Triglycerol (BRTG): 135 g
[0301] 50% NaOH in water: 0.82 g
[0302] The triglycerol was prepared by polymerisation in the same
manner as described in Example 1 except the refractive index was at
25.degree. C. was changed from 1.4855 to 1.4935.
[0303] 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-up.
[0304] Pressure is lowered to 50-100 mBar when the mixture reaches
235.degree. C. and is clear. Temperature is raised from room
temperature to 235.degree. C. in 50 min. The reaction mixture is
held at 235.degree. C. for 2.5 h, then cooled to 100.degree. C. and
pressure equalised with nitrogen. The product is clear.
[0305] Analysis: Acid value: 0.1; Saponification value: 144.9;
Hydroxyl value: 241.4; Alcaline number: 5.0
[0306] PGE 2680/073 with polyol 13%;
[0307] Rapeseed oil: 500 g
[0308] Broad Range Triglycerol (BRTG): 75 g
[0309] 50% NaOH in water: 0.8 g
[0310] The triglycerol was prepared by polymerisation in the same
manner as described in Example 1 except the refractive index was at
25.degree. C. was changed from 1.4855 to 1.4935,
[0311] 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-up.
[0312] Pressure is lowered to 50-100 mBar when the mixture reaches
235.degree. C. and is clear. Temperature is raised from room
temperature to 235.degree. C. in 50 min. The reaction mixture is
held at 235.degree. C. for 2.5 h, then cooled to 100.degree. C. and
pressure equalised with nitrogen. The product is clear.
[0313] Analysis: Acid value: 0.2; Saponification value: 163.9;
Hydroxyl value: 147.5; Alcaline number: 3.7
[0314] Polyol Distribution
[0315] 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.
TABLE-US-00004 TABLE 3 Polyol duplicate analysis Polyol % Analysis
Analysis Average of based on 1 2 2 Analyses total Polyols %
Glycerol 11.08 10.9998 11.03 % CY-Diglycerol 6.42 6.37 6.4 7.19% %
Diglycerol 21.56 21.51 21.54 24.20% % CY-Triglycerol 2.96 3 2.98
3.35% % Triglycerol 17.74 17.89 17.8182 20.02% % CY-Tetraglycerol
1.98 2.06 2.02 2.27% % Tetraglycerol 11.52 11.79 11.6566 13.10% %
CY-Pentaglycerol 2.78 2.7 2.74 3.08% % Pentaglycerol 6.8 6.93 6.87
7.72% % Hexaglycerol 6.53 6.67 6.6 7.42% % Heptaglycerol 4.84 4.89
4.87 5.47% % Octaglycerol 3.15 3 3.07 3.45% % Nonaglycerol 1.9 1.62
1.76 1.98% % Decaglycerol 0.74 0.58 0.66 0.74% % Undecaglycerol 0 0
0 0.00%
[0316] 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.
TABLE-US-00005 TABLE 4 BRHG/BRTG: Broad range Hexa/Tri-Glycerol
Polyol Oil Sample type Wt. % Polyol 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
[0317] The difference in polyol composition is shown below
[0318] 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.
TABLE-US-00006 TABLE 5 polyol distribution of samples REF PGE BRTG
BRHG % Glycerol 0.1 11 5.2 % CY-Diglycerol 0 6.4 9 % Diglycerol 27
21.5 9.7 % CY-Triglycerol 2.5 3 5.7 % Triglycerol 44.2 17.8 10.3 %
CY-Tetraglycerol 4.1 2 4 % Tetraglycerol 12.4 11.7 8.5 %
CY-Pentaglycerol 1.6 2.7 4.1 % Pentaglycerol 4.2 6.9 6.8 %
Hexaglycerol 2.5 6.6 9.2 % Heptaglycerol 1.2 4.9 8.5 % Octaglycerol
0 3.1 7 % Nonaglycerol 0 1.8 5.4 % Decaglycerol 0 0.7 3.6 %
Undecaglycerol 0 0 3.1
[0319] The viscosity of each emulsifier was measured on a Physica
Rheometer using the following setup:
[0320] Temp: 60.degree. C. to -10.degree. C. (1.degree. C./min),
Shear rate: 23 1/s, Measuring system: DG26.7 7-SN711; d=0 mm
[0321] Selected emulsifiers (REF PGE, J2680/060, J2680/065,
J2680/073) were further tested in WIF-emulsions with 50% water
content at 55.degree. C. at 0.1% and 0.2% dosage. Diesel quality:
MGO.
[0322] WIF-samples were prepared as described in Example 1.
[0323] Results
[0324] The droplet size distribution is shown in Table 6 and
graphically in FIG. 9 for D50.0 values. Samples 2680/065 and
2680/073 were not stable enough to allow NMR measurement.
TABLE-US-00007 TABLE 6 water droplet size distribution Dosage D2.5
D50.0 Sample % .mu.m .mu.m comments 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
[0325] The CLSM pictures of the emulsion are shown in FIG. 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.
[0326] The CLSM images of FIG. 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.
[0327] Sedimentation and water phase separation after 1 h, 2, and 3
h storage at 55.degree. C. for sample 2680/073 are shown in FIG.
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
[0328] Images of the emulsions are shown in FIG. 14.
[0329] 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.degree. C. is shown in FIG. 13.
[0330] 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
* * * * *