KR20140061366A - Composition - Google Patents

Abstract

(A) a fuel and (b) a polyglycerol ester of a fatty acid, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises from 11.0 to 34.0 wt.%, Based on the total weight of the polyglycerol, Positive diglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And a mixture of undeca glycerol in an amount of 0.0 to 7.0 weight percent based on the total weight of the polyglycerol.

Description

Composition {COMPOSITION}

The present invention relates to compositions. In particular, the present invention relates to a fuel composition having reduced nitrogen oxide emissions upon combustion.

As discussed in US 7,491,247, there is an increasing need to reduce nitrogen oxide (NOx) production due to environmental considerations and government regulations. Nitrogen oxides constitute the main stimulant in smog, which is believed to contribute to tropospheric ozone, which is known to be a health hazard. The relatively high flame temperature reached in an internal combustion engine, for example a diesel-fueled engine, increases the tendency to produce nitrogen oxides (NOx). These are formed from both the combination of nitrogen and oxygen in the combustion chamber and the oxidation of organic nitrogen species in the fuel.

Various methods for reducing NOx production include the use of catalytic converters, changes in engine timing, exhaust recirculation, and combustion of "clean" fuels. These methods are generally too costly and / or too complicated to apply to a wide range of applications. The rate at which NOx is formed is related to the flame temperature; A small decrease in flame temperature can greatly reduce nitrogen oxide production.

Although it has been shown that introducing water into the combustion zone can reduce flame temperatures and thus reduce NOx production, direct injection of water requires a costly and complex engine design change. A further attempt to reduce flame temperature using water involves the use of aqueous fuel, i.e., both water and fuel, into the emulsion. Problems that can arise from long term use of aqueous fuel include precipitate deposits, which include ionic species associations that cause filter plugging and deposits after inorganic combustion that generate turbo fouling. Another problem associated with aqueous fuel compositions is that they often require significant engine modifications, such as the addition of in-line homogenizers, thereby limiting their commercial usefulness.

Another way of introducing water into the combustion zone is to use a fuel emulsion, i.e. an invert fuel emulsion, in which water is emulsified in the fuel continuous phase. A problem associated with these reverse fuel emulsions is to obtain and maintain the stability of the emulsion under normal use conditions. Gravity separation (during storage) and high temperature high pressure / shear flow phase separation (during engine operation) of these emulsions are major obstacles to their commercial use.

DE-A-3229918 teaches the preparation of emulsions of 25 wt.% In diesel oil using emulsifiers which are polyesters of saturated or unsaturated fatty acids having 8 to 22 carbon atoms. Emulsifiers include polyglycerol esters, sorbitan esters or diacetyltartaric esters of glycerol esters of fatty acids. The emulsifier is applied in the fuel composition in an amount of from 0.65 to 1.6% by weight. Diesel emulsions are stable for more than six months and are taught to provide superior fuel economy, less coke deposition, and lower CO and hydrocarbon content in exhaust gas compared to pure diesel oil used in engines. In such a system, the emulsifier may be the most expensive component, and a high level of application in this document, such as 1.6 wt%, is expensive and not commercially practical in use.

The present invention solves the problems associated with the use of fuel emulsion compositions by providing a stable fuel emulsion composition with beneficial NOx emission reduction using commercially practicable amounts of emulsifiers.

The present invention alleviates the problems of the prior art.

In one aspect,

(a) fuel; And

(b) Polyglycerol esters of fatty acids

Wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is < RTI ID = 0.0 >

Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And 0.0 to 7.0% by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI > based on the total weight of the fuel composition.

In one aspect, the present invention provides a method of making a polyglycerol ester composition comprising mixing a polyglycerol ester of (a) a fuel and (c) water and (b) a fatty acid, wherein the polyglycerol composition used to form the polyglycerol ester

Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And 0.0 to 7.0% by weight, based on the total weight of polyglycerol, of undecaglycerol

Wherein the fuel and water-containing fuel composition comprises a mixture of the fuel and the water.

In one aspect, the present invention is directed to a process for preparing a fuel composition as defined herein, comprising a polyglycerol ester of a fatty acid as described herein, together with instructions for use in preparing a fuel composition comprising fuel and water The kit comprising:

In one aspect, the present invention provides a polyglycerol composition for use in forming polyglycerol esters of fatty acids,

Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And 0.0 to 7.0% by weight, based on the total weight of polyglycerol, of undecaglycerol

Of a polyglycerol ester of the fatty acid to improve the stability of the fuel and water-containing fuel composition.

The present inventors have found that when using a polyglycerol composition in which one polyglycerol predominantly exists such as diglycerol or triglycerol, the polyglycerol composition must be present in a considerably large amount to provide a stable fuel / water emulsion during storage I found out. On the other hand, the present inventors have surprisingly found that the presence of a wide range of polyglycerols in the polyglycerol composition, particularly in the specific ranges referred to herein, provides less fuel and water emulsion while still providing stable fuel and water emulsions over the period required for use, , And also that a commercially practicable amount of emulsifier can be used accordingly. The "flat" distribution of polyglycerols allows for these enhanced effects at low doses. The flattening distribution means that the polyglycerol has a broad polyglycerol chain length and the broad polyglycerol is present in an amount such that only some of the polyglycerols is dominant in the distribution of the polyglycerols. For example, in a flattening distribution, the length of one or two polyglycerol chains does not constitute 70 or 80% of the total amount of polyglycerols.

Now, for ease of reference, these and further aspects of the invention will be discussed under the appropriate section headings. However, the teaching under each section is not necessarily limited to each particular section.

Composition

As mentioned above, in one aspect,

(a) fuel; And

(b) Polyglycerol esters of fatty acids

Wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is < RTI ID = 0.0 >

Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And 0.0 to 7.0% by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI > based on the total weight of the fuel composition.

Fatty Polyglycerol  ester

As will be appreciated by those skilled in the art, polyglycerol esters of fatty acids are emulsifiers that contain polyglycerol ' backbone ' coupled with fatty acid side chains.

Polyglycerol esters of fatty acids are typically prepared by polymerizing glycerol to provide one or more polyglycerols followed by attachment of a fatty acid thereto. Fatty acids are generally combined in one of two ways. The first method involves direct binding of fatty acids to polyglycerol. The second scheme involves the transfer of fatty acids from triglycerides to polyglycerols by the mutual esterification of polyglycerol and triglycerides. Polymerization of glycerol typically provides a mixture of polyglycerols having different degrees of polymerization. Mixtures of polyglycerols having different degrees of polymerization are described herein as polyglycerol compositions. Those skilled in the art will understand that reference to a polyglycerol composition having a particular polyglycerol component merely requires that these ingredients be present in the specified amounts. One of ordinary skill in the art will recognize that due to the polymerization nature of glycerol, the polyglycerol composition may contain other polyglycerols having a degree of polymerization not mentioned herein. In determining the amount of polyglycerol in the polyglycerol composition, the total amount of all polyglycerols (regardless of degree of polymerization) is determined to provide the total weight of the polyglycerol composition. Materials that are not polyglycerol do not form part of the polyglycerol composition, and their weight is not taken into account when determining the total weight of the polyglycerol composition.

The phrase "total weight of polyglycerols" in this specification includes the total weight of all polyglycerols, regardless of their chain length, and whether or not polyglycerol is mentioned in the list of polyglycerols.

As discussed herein, the polyglycerol composition used to form the polyglycerol ester of a fatty acid includes diglycerol in an amount of 11.0 to 34.0 weight percent, based on the total weight of the polyglycerol; Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol; Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol; Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol; Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol; Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol; Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol; Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol; Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And a mixture of undeca glycerol in an amount of 0.0 to 7.0 weight percent based on the total weight of polyglycerol.

One of ordinary skill in the art will recognize that polyglycerols may be present in the form of cyclic polyglycerols or acyclic polyglycerols. Non-cyclic polyglycerols are straight chain and branched chain polyglycerols, i.e., non-cyclic polyglycerols are formed entirely from glycerol groups such that no ring is formed. Cyclic polyglycerol has a cyclic structure. As used herein, reference to polyglycerols having a certain degree of polymerization, such as triglycerol, which indicates polyglycerols having a degree of polymerization of 3, includes both polyglycerols in cyclic and non-cyclic forms. The inventors have also determined the preferred amounts of cyclic and non-cyclic polyglycerols for each of diglycerol, triglycerol, tetraglycerol and pentaglycerol. In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of from 6.0 to 25.0 wt%, based on the total weight of the polyglycerols, and cyclic amines in an amount of 5.0 to 13.0 wt% based on the total weight of the polyglycerols Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerides in an amount of 7.0 to 21.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of 2.5 to 9.5 weight percent, based on the total weight of the polyglycerols. Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of from 5.5 to 15.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of from 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in the amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in the amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect,

The diglycerol comprises non-cyclic diglycerol in an amount of from 6.0 to 25.0 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 5.0 to 13.0 wt% based on the total weight of the polyglycerol, ;

Triglycerol comprises non-cyclic triglycerol in an amount of 7.0 to 21.0 weight percent, based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 9.5 weight percent, based on the total weight of the polyglycerol, ;

Tetraglycerol comprises cyclic tetraglycerol in an amount of from 5.5 to 15.0 wt% based on the total weight of polyglycerol, and cyclic tetraglycerol in an amount of from 0.5 to 8.0 wt% based on the total weight of polyglycerol ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerol, and cyclic pentaglycerol, in an amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerol .

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of 6.0 to 15.0 wt% based on the total weight of the polyglycerols, and cyclic amines in an amount of 5.0 to 13.0 wt% based on the total weight of the polyglycerols Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerol in an amount of from 7.0 to 15.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerides in an amount of from 2.5 to 9.5 weight percent, based on the total weight of the polyglycerol, Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of 5.0 to 13.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in the amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in the amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of 6.0 to 15.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in the amount of 5.5 to 13.0 weight percent, based on the total weight of the polyglycerols Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerol in an amount of from 7.0 to 15.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerides in an amount of from 2.5 to 9.5 weight percent, based on the total weight of the polyglycerol, Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of 5.0 to 13.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in the amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in the amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect,

The diglycerol comprises non-cyclic diglycerol in an amount of from 6.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 5.5 to 13.0 wt% based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of from 7.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of from 2.5 to 9.5 wt% based on the total weight of the polyglycerol, ;

The tetraglycerol comprises cyclic tetraglycerol in an amount of from 5.0 to 13.0 weight percent, based on the total weight of the polyglycerol, and cyclic tetraglycerol, in an amount of from 0.5 to 8.0 weight percent, based on the total weight of the polyglycerol, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerol, and cyclic pentaglycerol, in an amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerol .

In one preferred aspect,

The diglycerol comprises non-cyclic diglycerol in an amount of from 6.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 5.5 to 13.0 wt% based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of from 7.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of from 2.5 to 9.5 wt% based on the total weight of the polyglycerol, ;

The tetraglycerol comprises cyclic tetraglycerol in an amount of from 5.0 to 13.0% by weight, based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 1.0 to 8.0% by weight, based on the total weight of the polyglycerol, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 3.0 to 11.0 weight percent, based on the total weight of the polyglycerol, and cyclic pentaglycerol, in an amount of 0.5 to 8.0 weight percent, based on the total weight of the polyglycerol .

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Non-cyclic diglycerol in an amount of from 6.0 to 15.0 wt% based on the total weight of polyglycerol, and cyclic diglycerol in an amount of from 5.5 to 13.0 wt% based on the total weight of polyglycerol;

Cyclic triglycerol in an amount of 7.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 9.5 wt% based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol, and cyclic tetraglycerol in an amount of 0.5 to 8.0 wt% based on the total weight of polyglycerol;

Non-cyclic pentaglycerol in an amount of 3.0 to 11.0 wt% based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 0.5 to 8.0 wt% based on the total weight of the polyglycerol;

Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;

Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of 4.0 to 12.0% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 2.0 to 10.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of 0.5 to 8.0% by weight, based on the total weight of polyglycerol; And

0.0 >% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Cyclic diglycerol in an amount of from 6.0 to 15.0 wt% based on the total weight of polyglycerol, and cyclic diglycerol in an amount of from 5.0 to 13.0 wt% based on the total weight of polyglycerol;

Cyclic triglycerol in an amount of 7.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 9.5 wt% based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol, and cyclic tetraglycerol in an amount of 1.0 to 8.0 wt% based on the total weight of polyglycerol;

Non-cyclic pentaglycerol in an amount of 3.0 to 11.0 wt% based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 0.5 to 8.0 wt% based on the total weight of the polyglycerol;

Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;

Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of 4.0 to 12.0% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 2.0 to 10.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of 0.5 to 8.0% by weight, based on the total weight of polyglycerol; And

0.0 >% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises diglycerol in an amount of 15.0 to 23.5 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises triglycerol in an amount of from 13.5 to 20.5% by weight, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises tetraglycerol in an amount of 10.0 to 17.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises pentaglycerol in an amount of from 8.0 to 14.5 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of from 8.0 to 11.5% by weight, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of 7.5-11.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of 6.5 to 10.0 wt% based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of from 4.0 to 8.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of 1.5 to 6.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of 0.5 to 5.0 wt.%, Based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Diglycerol in an amount of 15.0 to 23.5% by weight, based on the total weight of polyglycerol;

Triglycerol in an amount of from 13.5 to 20.5% by weight, based on the total weight of polyglycerol;

Tetraglycerol in an amount of 10.0 to 17.0 wt% based on the total weight of polyglycerol;

Pentaglycerol in an amount of from 8.0 to 14.5% by weight, based on the total weight of polyglycerol;

Hexaglycerol in an amount of from 8.0 to 11.5% by weight, based on the total weight of polyglycerol;

Heptaglycerol in an amount of 7.5-11.0 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of 6.5 to 10.0% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 4.0 to 8.0 wt% based on the total weight of polyglycerol;

Decaglycerol in an amount of from 1.5 to 6.0% by weight, based on the total weight of polyglycerol; And

0.5 to 5.0% by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of from 8.0 to 12.5 wt%, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of from 7.5 to 11.0 wt% based on the total weight of the polyglycerols Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerides in an amount of 9.0 to 13.0 weight percent, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of 4.5 to 7.5 weight percent, based on the total weight of the polyglycerols. Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of from 7.5 to 11.0 weight percent, based on the total weight of the polyglycerols, and cyclic amines in an amount of from 2.5 to 6.0 weight percent, based on the total weight of the polyglycerols. And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in an amount of 5.0 to 9.0 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in an amount of 2.5 to 6.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect,

The diglycerol comprises non-cyclic diglycerol in an amount of from 8.0 to 12.5% by weight, based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 7.5 to 11.0% by weight, based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of 9.0 to 13.0 weight percent based on the total weight of polyglycerol and cyclic triglycerol in an amount of 4.5 to 7.5 weight percent based on the total weight of polyglycerol, ;

The tetraglycerol comprises non-cyclic tetraglycerols in an amount of 7.5 to 11.0 weight percent, based on the total weight of the polyglycerols, and cyclic tetraglycerol in an amount of 2.5 to 6.0 weight percent, based on the total weight of the polyglycerols, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 5.0 to 9.0 weight percent based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight percent based on the total weight of the polyglycerol .

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Cyclic diglycerol in an amount of from 8.0 to 12.5 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 7.5 to 11.0 wt% based on the total weight of the polyglycerol;

Cyclic triglycerol in an amount of 9.0 to 13.0 wt% based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 4.5 to 7.5 wt% based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of 7.5 to 11.0 wt% based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of 2.5 to 6.0 wt% based on the total weight of the polyglycerol; And

Cyclic pentaglycerol in an amount of 5.0 to 9.0 weight percent based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight percent, based on the total weight of the polyglycerol,

, ≪ / RTI >

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of from 8.0 to 11.5% by weight, based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of 7.5-11.0 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of 6.5 to 10.0 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises nonaglycerol in an amount of 4.0 to 8.0 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of 1.5 to 6.0 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of 0.5 to 5.0 wt% based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises diglycerol in an amount of 17.6 to 21.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises triglycerol in an amount of from 15.9 to 18.1 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises tetraglycerol in an amount of from 12.5 to 14.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises pentaglycerol in an amount of 10.5 to 12.2 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of 9.3 to 10.1 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of from 8.6 to 9.9 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of 7.3 to 8.9 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises nonaglycerol in an amount of 5.5 to 6.4 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of 2.9 to 4.5 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of 1.8 to 3.7% by weight, based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Diglycerol in an amount of 17.6 to 21.0% by weight, based on the total weight of polyglycerol;

Triglycerol in an amount of from 15.9 to 18.1% by weight, based on the total weight of polyglycerol;

Tetraglycerol in an amount of from 12.5 to 14.0% by weight, based on the total weight of polyglycerol;

Pentaglycerol in an amount of 10.5 to 12.2 wt% based on the total weight of polyglycerol;

Hexaglycerol in an amount of 9.3 to 10.1% by weight, based on the total weight of polyglycerol;

Heptaglycerol in an amount of from 8.6 to 9.9% by weight, based on the total weight of polyglycerol;

Octaglycerol in an amount of 7.3 to 8.9% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 5.5 to 6.4% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of 2.9 to 4.5% by weight, based on the total weight of polyglycerol; And

Based on the total weight of the polyglycerol, 1.8 to 3.7% by weight undecaglycerol

≪ / RTI >

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of 9.1 to 11.4 wt%, based on the total weight of the polyglycerols, and cyclic amines in an amount of 8.5 to 9.5 wt% based on the total weight of the polyglycerols Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerol in an amount of 10.0 to 11.8 wt%, based on the total weight of the polyglycerol, and cyclic triglycerides in an amount of 5.9 to 6.3 wt%, based on the total weight of the polyglycerol Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in the amount of from 8.4 to 9.5 wt%, based on the total weight of the polyglycerols, and cyclic triglycerides in the amount of 4.1 to 4.4 wt%, based on the total weight of the polyglycerols And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in the amount of 6.7 to 7.6 wt%, based on the total weight of the polyglycerols, and cyclic amines in the amount of 3.8 to 4.6 wt%, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect,

The diglycerol comprises non-cyclic diglycerol in an amount of 9.1 to 11.4 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 8.5 to 9.5 wt% based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of from 10.0 to 11.8% by weight, based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of from 5.9 to 6.3% by weight, based on the total weight of the polyglycerol, ;

Tetraglycerol comprises cyclic tetraglycerol in an amount of from 8.4 to 9.5% by weight, based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of 4.1 to 4.4% by weight, based on the total weight of the polyglycerol, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 6.7 to 7.6 wt% based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 3.8 to 4.6 wt% based on the total weight of the polyglycerol .

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Cyclic diglycerol in an amount of 9.1 to 11.4 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 8.5 to 9.5 wt% based on the total weight of the polyglycerol;

Cyclic triglycerol in an amount of 10.0 to 11.8 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 5.9 to 6.3 weight percent based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of from 8.4 to 9.5 wt% based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 4.1 to 4.4 wt% based on the total weight of the polyglycerol; And

Non-cyclic pentaglycerol in an amount of 6.7 to 7.6 wt% based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 3.8 to 4.6 wt% based on the total weight of the polyglycerol

, ≪ / RTI >

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of 9.3 to 10.1 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of from 8.6 to 9.9 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of 7.3 to 8.9 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises nonaglycerol in an amount of 5.5 to 6.4 wt% based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of from 2.9 to 4.5 weight percent, based on the total weight of the polyglycerol;

The polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of 1.8 to 3.7% by weight, based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises diglycerol in an amount of 18.0 to 32.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises triglycerol in an amount of from 16.0 to 24.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises tetraglycerol in an amount of 12.0 to 16.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises pentaglycerol in an amount of from 8.0 to 12.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of 7.0 to 11.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of from 5.0 to 10.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of from 3.0 to 9.0% by weight, based on the total weight of the polyglycerol. 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 percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of 0.0 to 4.5 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of from 0.0 to 4.0% by weight, based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Diglycerol in an amount of 18.0 to 32.0% by weight, based on the total weight of polyglycerol;

Triglycerol in an amount of 16.0 to 24.0% by weight, based on the total weight of polyglycerol;

Tetraglycerol in an amount of 12.0 to 16.0% by weight, based on the total weight of polyglycerol;

Pentaglycerol in an amount of from 8.0 to 12.0% by weight, based on the total weight of polyglycerol;

Hexaglycerol in an amount of 7.0 to 11.0 weight percent, based on the total weight of polyglycerol;

Heptaglycerol in an amount of 5.0 to 10.0 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of 3.0 to 9.0% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of from 1.5 to 7.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of 0.0 to 4.5% by weight, based on the total weight of polyglycerol; And

0.0 > 4.0% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of from 9.0 to 24.5% by weight, based on the total weight of the polyglycerols, and cyclic amines in an amount of 6.5 to 10.0% Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerides in an amount of from 9.0 to 20.5% by weight, based on the total weight of the polyglycerols, and cyclic triglycerides in an amount of from 3.5 to 6.5% Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of from 8.0 to 13.5% by weight, based on the total weight of the polyglycerols, and cyclic polyglycerols in an amount of from 2.0 to 4.5% And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in an amount of 6.0 to 9.0 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in an amount of 2.0 to 5.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect, in the polyglycerol composition used to form the polyglycerol ester of the fatty acid,

Diglycerol comprises cyclic diglycerol in an amount of from 9.0 to 24.5% by weight, based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 6.5 to 10.0% by weight, based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of from 9.0 to 20.5% by weight, based on the total weight of the polyglycerol, and from 3.5 to 6.5% by weight, based on the total weight of the polyglycerol, of cyclic triglycerol ;

The tetraglycerol comprises non-cyclic tetraglycerols in an amount of from 8.0 to 13.5% by weight, based on the total weight of the polyglycerols, and cyclic tetraglycerol in an amount of from 2.0 to 4.5% by weight, based on the total weight of the polyglycerols, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of from 6.0 to 9.0 weight percent based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of from 2.0 to 5.0 weight percent based on the total weight of the polyglycerol .

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Noncycled diglycerol in an amount of 9.0 to 24.5 weight percent based on the total weight of polyglycerol, and cyclic diglycerol in an amount of 6.5 to 10.0 weight percent based on the total weight of polyglycerol;

Cyclic triglycerol in an amount of 9.0 to 20.5 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 3.5 to 6.5 weight percent based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of from 8.0 to 13.5 wt% based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 2.0 to 4.5 wt% based on the total weight of the polyglycerol;

Cyclic pentaglycerol in an amount of 6.0 to 9.0 weight percent based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 2.0 to 5.0 weight percent based on the total weight of the polyglycerol;

Hexaglycerol in an amount of 7.0 to 11.0 weight percent, based on the total weight of polyglycerol;

Heptaglycerol in an amount of 5.0 to 10.0 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of 3.0 to 9.0% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of from 1.5 to 7.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of 0.0 to 4.5% by weight, based on the total weight of polyglycerol; And

0.0 > 4.0% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises diglycerol in an amount of 26.0 to 34.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises triglycerol in an amount of 21.0 to 25.0 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises tetraglycerol in an amount of 12.0 to 17.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises pentaglycerol in an amount of from 8.0 to 12.0 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises hexaglycerol in an amount of from 6.0 to 10.0% by weight, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises heptaglycerol in an amount of 4.5 to 7.5 weight percent, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises octaglycerol in an amount of 2.5 to 5.5 wt%, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises nonaglycerol in an amount of from 1.0 to 3.0% by weight, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises decaglycerol in an amount of from 0.0 to 1.0% by weight, based on the total weight of the polyglycerol. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid comprises undeca glycerol in an amount of from 0.0 to 0.5% by weight, based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises undeca glycerol in an amount of 0.0 to 0.01% by weight, based on the total weight of the polyglycerol.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Diglycerol in an amount of 26.0 to 34.0 wt% based on the total weight of polyglycerol;

Triglycerol in an amount of 21.0 to 25.0% by weight, based on the total weight of polyglycerol;

Tetraglycerol in an amount of 12.0 to 17.0% by weight, based on the total weight of polyglycerol;

Pentaglycerol in an amount of from 8.0 to 12.0% by weight, based on the total weight of polyglycerol;

Hexaglycerol in an amount of 6.0 to 10.0% by weight, based on the total weight of polyglycerol;

Heptaglycerol in an amount of 4.5 to 7.5 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of from 2.5 to 5.5% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 1.0 to 3.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of from 0.0 to 1.0% by weight, based on the total weight of polyglycerol; And

0.0 > 0.5% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

In one preferred aspect, the diglycerol is selected from the group consisting of non-cyclic diglycerols in an amount of from 20.0 to 26.0 weight percent, based on the total weight of the polyglycerols, and cyclic amines in an amount of 6.5 to 8.0 weight percent, based on the total weight of the polyglycerols. Diglycerol. In one preferred aspect, the triglycerol is selected from the group consisting of non-cyclic triglycerol in an amount of 18.0 to 21.0 weight percent, based on the total weight of the polyglycerol, and cyclic triglycerides in an amount of 2.5 to 5.0 weight percent, based on the total weight of the polyglycerol. Triglycerol. In one preferred aspect, the tetraglycerol is selected from the group consisting of non-cyclic tetraglycerols in an amount of 11.0 to 14.5 wt% based on the total weight of the polyglycerols, and cyclic amines in an amount of 1.5 to 4.0 wt% based on the total weight of the polyglycerols And tetraglycerol. In one preferred aspect, the pentaglycerol is selected from the group consisting of non-cyclic pentaglycerols in the amount of 6.5 to 9.5 weight percent, based on the total weight of the polyglycerols, and cyclic pentaglycerols in the amount of 1.5 to 4.0 weight percent, based on the total weight of the polyglycerols. Pentaglycerol.

In one preferred aspect, the triglycerol comprises non-cyclic triglycerol in an amount of 18.0 to 21.0 weight percent, based on the total weight of the polyglycerol.

In one preferred aspect, in the polyglycerol composition used to form the polyglycerol ester of the fatty acid,

The diglycerol comprises non-cyclic diglycerol in an amount of 20.0 to 26.0 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 6.5 to 8.0 wt% based on the total weight of the polyglycerol, ;

Triglycerol comprises cyclic triglycerol in an amount of from 18.0 to 21.0 wt.%, Based on the total weight of polyglycerol, and cyclic triglycerol in an amount of from 2.5 to 5.0 wt.%, Based on the total weight of polyglycerol, ;

The tetraglycerol comprises cyclic tetraglycerol in an amount of from 11.0 to 14.5 wt% based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 1.5 to 4.0 wt% based on the total weight of the polyglycerol, ;

The pentaglycerol comprises non-cyclic pentaglycerol in an amount of 6.5 to 9.5 wt% based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 1.5 to 4.0 wt% based on the total weight of the polyglycerol .

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid

Cyclic diglycerol in an amount of 20.0 to 26.0 wt% based on the total weight of polyglycerol, and cyclic diglycerol in an amount of 6.5 to 8.0 wt% based on the total weight of polyglycerol;

Cyclic triglycerol in an amount of 18.0 to 21.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 5.0 weight percent based on the total weight of the polyglycerol;

Cyclic tetraglycerol in an amount of 11.0 to 14.5 wt% based on the total weight of polyglycerol, and cyclic tetraglycerol in an amount of 1.5 to 4.0 wt% based on the total weight of polyglycerol;

Cyclic pentaglycerol in an amount of 6.5 to 9.5 weight percent based on the total weight of the polyglycerol, and cyclic pentaglycerol in an amount of 1.5 to 4.0 weight percent based on the total weight of the polyglycerol;

Hexaglycerol in an amount of 6.0 to 10.0% by weight, based on the total weight of polyglycerol;

Heptaglycerol in an amount of 4.5 to 7.5 wt% based on the total weight of polyglycerol;

Octaglycerol in an amount of from 2.5 to 5.5% by weight, based on the total weight of polyglycerol;

Nonaglycerol in an amount of 1.0 to 3.0% by weight, based on the total weight of polyglycerol;

Decaglycerol in an amount of from 0.0 to 1.0% by weight, based on the total weight of polyglycerol; And

0.0 > 0.5% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol

≪ / RTI >

The fatty acid side chain bonded to the polyglycerol may have any suitable length. The polyglycerol ester of the fatty acid may be a polyglycerol ester of a single fatty acid, or a polyglycerol ester of a mixture of fatty acids. The fat chain length of the fatty acid of the polyglycerol ester need not have the same length. Typically, polyglycerol esters of fatty acids are esters of fatty acids of C12 to C22 fatty acids. Preferably the polyglycerol ester of the fatty acid is an ester of a C16 or C22 fatty acid. Preferably the polyglycerol ester of the fatty acid is an ester of a C16 or C18 fatty acid. Preferably the polyglycerol ester of the fatty acid is an ester of a C18 fatty acid.

The fatty acid of the polyglycerol ester of the fatty acid may be a saturated fatty acid, an unsaturated fatty acid or a mixture of saturated and unsaturated fatty acids. In one aspect, the fatty acid of the polyglycerol ester of the fatty acid is an unsaturated fatty acid. The fatty acid of the polyglycerol ester of the fatty acid may be a mono- or di-unsaturated fatty acid. Preferably the fatty acid of the polyglycerol ester of the fatty acid is a mono-unsaturated fatty acid.

A highly preferred fatty acid of the polyglycerol ester of fatty acids is oleic acid ((9Z) -octadec-9-enoic acid).

The fatty acid bound to the polyglycerol may be provided from any suitable source. Thus, in one aspect, the polyglycerol fatty acid esters are prepared from fatty acids from oils selected from rapeseed oil, high oleic rapeseed oil, soybean oil, high oleic sunflower oil, tolle oil and mixtures thereof.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of 880 to 1230 mg KOH / g. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of 1130 to 1230 mg KOH / g. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of 880 to 1060 mg KOH / g. In a further preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of 950 to 990 mg KOH / g.

In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4860 to 1.4925 at 50 ° C. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4895 to 1.4925 at 50 ° C. In a further preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4900 to 1.4920 at 50 ° C. In a further preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4900 to 1.4910 at 50 ° C. In one preferred aspect, the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4855 to 1.4935 at 25 占 폚.

In one preferred aspect, the polyglycerol esters of fatty acids have a viscosity of less than 700 mPa s at 20 캜, such as less than 600 mPa s at 20 캜, such as less than 500 mPa s at 20 캜, such as less than 400 mPa s at 20 캜, Less than 350 mPa s, such as less than 300 mPa s at 20 ° C, such as less than 250 mPa s at 20 ° C, such as less than 200 mPa s at 20 ° C. The inventors have found that during manufacture of the fuel emulsion according to the present invention, a low viscosity as described above and preferably at 20 DEG C of less than 200 mPa s is an important factor in the production of effective emulsions.

The inventors have found that the means by which the viscosity of the polyglycerol ester of the fatty acid can be controlled is by controlling the ratio of the polyol to the triglyceride source in producing the polyglycerol ester of the fatty acid of the present invention as well as the fatty acid profile described in detail herein Respectively. The effect of the ratio of polyol to triglyceride source is shown in FIG. Thus, in one aspect, polyglycerol esters of fatty acids are prepared by reacting polyglycerol and fatty acid triglycerides in a ratio of polyglycerol to fatty acid triglyceride from 1: 1 to 1:10. Preferably the polyglycerol ester of a fatty acid is present in a ratio of from 1: 1 to 1: 9, such as from 1: 1: 1 to 1: 4 such as 1: 2 to 1: 4 such as 1: 2 to 1: 3 such as 1: Such as 1: 4 to 1: 7 such as 1: 4 to 1: 7 such as 1: 4 to 1: : 6 to 1: 7, such as approximately 1: 6.7, of polyglycerol to fatty acid triglycerides.

Fuel composition

When a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein is provided in accordance with the present invention, the polyglycerol ester can be added to the water and fuel composition in any suitable amount to provide an emulsion with the desired stability Can be applied. 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% by weight, 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 weight percent, 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 weight percent, based on the total fuel composition. In a further aspect, the fuel composition comprises a polyglycerol ester of a fatty acid made from a mixture of polyglycerols as described herein in an amount less than 0.5% by weight 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 less than 0.3% by weight 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 less than 0.25% by weight 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 less than 0.2 weight percent 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 less than 0.15% by weight, 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 less than 0.1% by weight, based on the total fuel composition.

As discussed herein, the present inventors have confirmed that by the use of a "flat" composition of polyglycerol, the emulsifier can be used in an amount less than that required in the prior art. Thus, in a preferred aspect, the polyglycerol ester of the fatty acid is present in an amount less than 0.5% by weight. The enhanced activity of the composition of the polyglycerol esters of the present invention allows the emulsifier to be applied in a smaller amount than previously required in the prior art. This is advantageous both for cost reasons and also for storage. These materials are applied during use and should therefore be transported by the user. Minimizing the amount of material required to achieve the desired effect is important to the end user. While the compositions of the present invention enable lower levels of use than the prior art, the compositions of the present invention may be applied at any level, e.g., at a higher level in a desired application. One skilled in the art will appreciate that polyglycerol esters of fatty acids can be applied in any amount depending on the application desired and the desired stability time.

fuel

As discussed herein, the emulsifiers described allow for the production of emulsions of fuels and water. Fuels suitable for being made into emulsions but still to be combined with water are included herein by the present invention. However, in a preferred aspect, the fuel containing the emulsifier is combined with water, and the fuel composition further comprises (c) water. In this regard, it will be appreciated that the fuel composition may be prepared by first applying a polyglycerol ester of fatty acid in a fuel, such as marine gas oil (MGO), and then applying water to the fuel / emulsifier blend.

The amount of water can be selected based on the requirements of the combustion system. In one aspect, the fuel composition further comprises (c) water in an amount of 10 to 70 weight percent, based on the total fuel composition. Preferably water is present in an amount of 30 to 60 wt.% Based on the total fuel composition. Preferably water is present in an amount of from 33 to 50% by weight, based on the total fuel composition.

The compositions 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 combustion system performance. Suitable additives include, but are not limited to, detergents, carrier oils, antioxidants, corrosion inhibitors, color stabilizers, metal deactivators, cetane number improvers, other combustion improvers, defoamers, pour point depressants, low temperature filter clogging point depressants, , Soot inhibitors, lubricants, and other particulate filter regeneration additives.

The fuel may be any fuel suitable for combustion in which reduction of NOx is desired. In one aspect, the fuel is a fuel for a spark ignition engine, 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 gas oil (MGO) and kerosene. Diesel can be biodiesel, low sulfur diesel and ultra low sulfur diesel. Preferably the fuel is marine gas oil. The marine gas oil may be any suitable offshore gas oil. In one aspect, it comprises: (i) a density of 0.85 to 0.89 g / cm ³ , a cetane number of about 45; And a flash point of greater than 55 < 0 > C.

Aspects of the invention are defined in the appended claims.

Now, the present invention will be described in more detail in the following examples, wherein

Figures 1, 3a, 3b, 7 to 9 and 13 show graphs;

Figures 2, 3c, 4, 5, 6, 10, 11, 12 and 14 represent images.

Example

Example  One

Four polyglycerol esters were prepared and tested. Two were broad polyglycerol (BRPG) esters according to the invention, one of which was based on soybean oil and the other one was based on oleic acid. The two species were triglycerol esters prepared as comparative examples, one species being based on soybean oil, and one species being based on oleic acid.

Preparation of polyglycerol :

Glycerol: 1250 kg

50% NaOH in water: 9.17 kg

) 측정을 위해 반응기로부터 회수하였다. Glycerol and NaOH solution were added to the reactor. Using a column and a condenser, the mixture was heated to 240 ° C, taking care not to distill the glycerol. Heating to 240 ° C took about 3 hours. The pressure was then carefully lowered to about 30 mbar to remove the reaction water from the polymerization of the glycerol. After about 7 to 14 hours at < RTI ID = 0.0 > 240 C, < / RTI >

) ≪ / RTI >

The refractive index was used to determine the termination of the reaction. The refractive index should be within the range of 1.4900 to 1.4920. If the index of refraction is still not within the interval, the reaction is continued for an additional hour and another sample is collected for measurement. This was continued until the refractive index was within the interval. When the polyglycerol was in the intermittent-interval, the temperature was lowered to 120 ° C.

The glycerol and polyglycerol contents of the BRPG samples were measured. The details of this analysis are described below.

Details of the hydroxyl value and the refractive index for the wide range polyglycerol and triglycerol of the present invention used in the ester are described below.

Broad polyglycerol

Hydroxyl value (OHV): 950 to 990

Refractive index at 50 占 폚: 1.4900 to 1.4920

Triglycerol

Hydroxyl value (OHV): 1090 to 1190

Refractive index (20 캜): 1.4930 to 1.4970

Preparation of triglycerol and polyglycerol ester:

Polyglycerol PGE 2440/198:

Soybean oil: 700 g

Polyglycerol: 203.2 g

50% NaOH in water: 3.80 g

Polyglycerol was prepared according to the above method.

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

The temperature was raised to 90 占 폚. When the mixture reached 90 캜, the pressure was dropped to about 50 mBar. The temperature was then increased to 230 DEG C and held at this temperature for 30 minutes. Lt; 0 > C. The pressure was equalized with nitrogen at < RTI ID = 0.0 > 90 C. < / RTI > The product was clean.

Analysis: acid value: 0.3; Saponification value: 146.2; Hydroxyl value: 219.2.

Polyglycerol PGE  2526/160:

Oleic acid 90%: 340 g

Polyglycerol: 102 g

Glycerol: 37 g

50% NaOH in water: 1.75 g

Polyglycerol was prepared according to the above method.

All components were charged to a three-necked flask equipped with a mechanical stirrer, Vigreux column, condenser, thermostat, nitrogen protection, and vacuum pump connected to the setup.

The temperature was gradually increased to 235 ° C. The reaction water was distilled at 208 占 폚. After 80 min, the mixture was clean and the temperature was 235 ° C. The reaction mixture was allowed to react for an additional 1 h.

The pressure was gradually reduced to 75 mBar. The mixture was then allowed to react for an additional 1 h. Samples were collected for acid value determination.

When the acid value was less than 2, the product was finished and the temperature was lowered to 90 占 폚. The pressure was equalized with nitrogen. The product was clean.

Analysis: Acid value: 0.5; Saponification value: 145.5; Hydroxyl value: 214.9; Alkali value: 7.4.

Triglycerol PGE 2528/072 (comparative):

Soybean oil: 700 g

Triglycerol: 215 g

50% NaOH in water: 3.80 g

Triglycerol was obtained from Solvay.

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

When the mixture reached 90 캜, the pressure was dropped to about 50 mBar. The temperature was raised from room temperature to 230 캜 within 85 min. The reaction mixture was maintained at 230 占 폚 for 2.5 hours, then cooled to 90 占 폚, and the pressure was equalized with nitrogen. The product was clean.

Analysis: acid value: 0.2; Saponification value: 142.6; Iodine Value: 95.2; Color 5 1/4 ", total: 3.0 yellow: 15 red: 1.5.

Triglycerol PGE 2526/159 (comparative):

Oleic acid 90%: 340 g

Triglycerol: 108 g

Glycerol: 37 g

50% NaOH in water: 1.75 g

Triglycerol was obtained from Solvay.

All components were charged to a three-necked flask equipped with a mechanical stirrer, Vigreux column, condenser, thermostat, nitrogen protection, and vacuum pump connected to the setup.

The temperature was gradually increased to 235 ° C. The reaction water was observed at 208 ° C. After 65 min, the mixture was clean and the temperature was 235 ° C. The reaction mixture was allowed to react for an additional 1 h. The pressure was gradually lowered to 75 mBar, and the mixture was then allowed to react for an additional 1 h. Samples were collected for acid value determination. When the acid value was less than 2, the product was finished and the temperature was lowered to 90 占 폚. The pressure was equalized with nitrogen. The product was clean.

Analysis: acid value: 0.8; Saponification value: 143.6; Hydroxyl value: 262.8; Alkali value: 4.6.

Four polyglycerol esters based on soybean oil or oleic acid and triglycerol or broad polyglycerol (BRPG) esters were prepared with a 50% water content at 55 ° C with a focus on the hydrodynamic size distribution, stability and emulsion viscosity Fuel-in-water-emulsion (WIF-emulsion).

The results show that BRPG esters provide less water droplets and reduced water droplet sedimentation during storage than the triglycerol ester.

Four samples with two polyol distributions (triglycerol vs. BRPG) and two fatty acid sources (soybean oil vs. pure oleic acid) were tested. The main focus of the test was the effect of reduced emulsifier addition on emulsion stability.

Experiment

Four emulsifiers were tested in a fuel-in-water emulsion, WIF-emulsion, having a 50% water content at 55 占 폚. Emulsifiers are listed in Table 1. The application amount was 0.5%, 0.25% and 0.1% based on the emulsion. The emulsion (200 g) was prepared by slowly adding the aqueous phase to the fuel (MGO) during homogenization at 20500 rpm for 64 s using an Ultra Turrex. Both MGO and water were heated to 55 < 0 > C and emulsified.

Immediately following emulsion preparation, the following analysis was performed.

1. Water droplet size distribution by NMR.

2. Microscopic examination by CLSM.

3. Emulsion stability during storage for 3 hours at 55 ° C by imaging and image analysis.

The marine gas oil (diesel) used in the test was Shell Thermo heated oil.

result

The water droplet size distribution is shown in Table 2. Note the significant increase in the liquid droplet size at low emulsifier concentrations.

The D50.0 values are compared in FIG. 1, where a large increase in droplet size at the 0.1% application level is evident. The graph also shows that PGE based on BRPG (broad polyglycerol) provides a smaller water droplet compared to triglycerol based PGE in highly stressed conditions (0.1% emulsifier application amount). At the same time, PGE based on fatty acids from soybean oil provides larger droplets compared to PGE based on pure oleic acid.

The droplet size distribution by CLSM is compared with the application amount of 0.5% and 0.1% emulsifier. A large increase in droplet size at low emulsifier applications is evident in the figure. A photograph of a sample with 0.25% emulsifier addition is shown in FIG. A photograph of a sample with addition of 0.1%, 0.25% and 0.5% emulsifier is shown in FIG.

Figures 3a, 3b and 3c show the degree of water droplet sedimentation in the emulsion during storage for 3 hours at 55 占 폚 with addition of 0.5%, 0.25% and 0.1% emulsifier. The degree of settling is expressed as a percentage of the total sample height of the free diesel oil on the sample. The value is generated by image analysis.

Note the difference in degree of sedimentation between the levels of application. At 0.1% coverage, sedimentation is 10 times greater than at the 0.5% coverage level.

The esters of triglycerol and soybean oil have poor performance at low concentrations. Thus, the performance of this emulsifier is more sensitive to the reduction in application than the broad range polyglycerol ester emulsifiers of the present invention.

At low concentrations, the two emulsifiers based on the BRPG of the present invention have better performance than triglycerol based emulsifiers. This is in agreement with the difference in the water droplet size shown in Fig.

A photograph of the sample can be seen in Figures 4 and 5.

conclusion

It has been clearly demonstrated that polyglycerol esters based on broad polyglycerol provide less water droplets and reduced water droplet sedimentation during storage than polyglycerol esters based on triglycerol. These effects appeared in very small (0.1%) additions of emulsifiers indicating stress conditions, which is most similar to real life situations. In addition, it has been concluded that a fatty acid composition having a high oleic acid content based on the above characteristics is superior to a composition having a high linoleic acid (soybean oil).

Example 2

An additional four polyglycerol esters were prepared and tested. Each was a broad polyglycerol (BRPG) ester according to the invention, each based on rapeseed oil. Two were triglycerol esters and two were hexaglycerol esters.

The esters according to the invention were compared with the comparative examples prepared from triglycerol and soybean oil (REF PGE or REF).

Experiment

PGE 2680/060 with 13% polyol:

Plain seed oil: 920 g

Extensive hexaglycerol (BRHG): 138 g

50% NaOH in water: 1.92 g

Hexaglycerol was prepared by polymerization in the same manner as described in Example 1. < tb > < TABLE >

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

When the mixture reached < RTI ID = 0.0 > 235 C < / RTI > and was cleaned, the pressure was lowered to 50-100 mBar. The temperature was raised from room temperature to 235 캜 within 50 min. The reaction mixture was maintained at 235 캜 for 2.5 h, then cooled to 100 캜, and the pressure was equalized with nitrogen. The product was clean.

Analysis: acid value: 0.2; Saponification value: 161.8; Hydroxyl value: 125; Alkali value: 3.9

PGE 2680/065 with 10% polyol:

Plain seed oil: 960 g

Broad hexaglycerol (BRHG): 106.6 g

50% NaOH in water: 2.4 g

Hexaglycerol was prepared by polymerization in the same manner as described in Example 1. < tb > < TABLE >

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

When the mixture reached < RTI ID = 0.0 > 235 C < / RTI > and was cleaned, the pressure was lowered to 50-100 mBar. The temperature was raised from room temperature to 235 캜 within 50 min. The reaction mixture was maintained at 235 캜 for 2.5 h, then cooled to 100 캜, and the pressure was equalized with nitrogen. The product was clean.

Analysis: acid value: 0.2; Saponification value: 168.6; Hydroxyl value: 100.2; Alkali value: 4.1

PGE 2680/062 with 23% polyol:

Plain seed oil: 450 g

Broad triglycerol (BRTG): 135 g

50% NaOH in water: 0.82 g

Triglycerol was prepared by polymerization in the same manner as described in Example 1 except that the refractive index was at 25 캜 and changed from 1.4855 to 1.4935.

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

When the mixture reached < RTI ID = 0.0 > 235 C < / RTI > and was cleaned, the pressure was lowered to 50-100 mBar. The temperature was raised from room temperature to 235 캜 within 50 min. The reaction mixture was maintained at 235 캜 for 2.5 h, then cooled to 100 캜, and the pressure was equalized with nitrogen. The product was clean.

Analysis: Acid value: 0.1; Saponification value: 144.9; Hydroxyl value: 241.4; Alkali value: 5.0

PGE 2680/073 with 13% polyol:

Plain seed oil: 500 g

Broad triglycerol (BRTG): 75 g

50% NaOH in water: 0.8 g

Triglycerol was prepared by polymerization in the same manner as described in Example 1 except that the refractive index was at 25 캜 and changed from 1.4855 to 1.4935.

All components were charged to a three-necked flask equipped with a mechanical stirrer, condenser and thermostat, using nitrogen protection, and a vacuum pump connected to the setup.

When the mixture reached < RTI ID = 0.0 > 235 C < / RTI > and was cleaned, the pressure was lowered to 50-100 mBar. The temperature was raised from room temperature to 235 캜 within 50 min. The reaction mixture was maintained at 235 캜 for 2.5 h, then cooled to 100 캜, and the pressure was equalized with nitrogen. The product was clean.

Analysis: acid value: 0.2; Saponification value: 163.9; Hydroxyl value: 147.5; Alkali value: 3.7

Distribution of polyols

2680/062, and 2680/073, respectively. Analysis was performed twice and the mean was determined. The results of this analysis are shown in Table 3 below.

The synthesized polyglycerol esters are summarized in Table 4. Three polyglycerols were included in the series, two of which were triglycerol and one of hexaglycerol. The fatty acid source was soybean oil or rapeseed oil.

The difference in the polyol composition is shown below.

The distribution of polyols of BRHG used in the preparation of sample REF PGE, 2680/073 and of BRHG used in the preparation of 2680/060 is shown in Table 5.

The viscosity of each emulsifier was measured on a Physica Rheometer using the following setup.

Temperature: 60 캜 to -10 캜 (1 캜 / min), shear rate: 23 1 / s, measurement system: DG26.7 7-SN711; d = 0 mm

The selected emulsifier (REF PGE, J2680 / 060, J2680 / 065, J2680 / 073) was further tested in a WIF-emulsion with a 50% water content at 55 DEG C in 0.1% and 0.2% Diesel Quality: MGO.

A WIF-sample was prepared as described in Example 1.

result

The droplet size distribution is shown in Table 6, and the D50.0 value is shown graphically in FIG. Samples 2680/065 and 2680/073 were not stable enough to allow NMR measurements.

A CLSM photograph of the emulsion is shown in Fig. Images were recorded immediately after emulsification. Both Samples 2680/065 and 2680/073 provide much larger water droplets at both levels of emulsifier application compared to the reference (REF PGE) and 2680/060.

The CLSM image of Figure 11 shows a dramatic increase in the droplet size at low emulsifier application, as samples 2680/065 and 2680/073, as a symptom of reduced functionality. Also, at the 0.2% application level, the droplet is apparently larger than the sample REF PGE and 2680/060.

Settling and aqueous phase separation after 1 h, 2, and 3 h storage at 55 ° C for sample 2680/073 are shown in FIG. This prominent water separation is uncommon in WIF-emulsions. However, settling during rest is not a problem since the homogeneous emulsion will be reformed during flow.

An image of the emulsion is shown in Fig.

The degree of water droplet precipitation in the emulsion, expressed as the amount of upper glass oil formed during storage for 3 hours at 55 DEG C, is shown in Fig.

All publications mentioned in the above specification are incorporated herein by reference. Various changes and modifications to the described method and system of the present invention will be apparent to those skilled in the art without departing from the scope and spirit of the invention. While the invention has been described in connection with specific preferred embodiments, it is to be understood that the invention as claimed should not be unduly limited to such specific embodiments. Indeed, various changes to the manner of practicing the invention, which are apparent to those skilled in the chemical or related art, are intended to be included within the scope of the following claims.

Claims (38)

(a) fuel; And
(b) Polyglycerol esters of fatty acids
Wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is < RTI ID = 0.0 >
Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol;
Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;
Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And
0.0 > 7% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol
≪ / RTI > The composition of claim 1, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is
Diglycerol in an amount of 11.0 to 28.0 wt% based on the total weight of polyglycerol;
Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;
Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of 4.0 to 12.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of 2.0 to 10.0% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 0.5 to 8.0% by weight, based on the total weight of polyglycerol; And
0.0 >%< / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol
≪ / RTI > The method according to claim 1,
Wherein the diglycerol is selected from the group consisting of acyclic diglycerol in an amount of 6.0 to 25.0 weight percent based on the total weight of the polyglycerol and cyclic diglycerol in an amount of 5.0 to 13.0 weight percent based on the total weight of polyglycerol / RTI >
Wherein the triglycerol comprises non-cyclic triglycerol in an amount of 7.0 to 21.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 9.5 weight percent based on the total weight of the polyglycerol, ;
Tetraglycerol comprises cyclic tetraglycerol in an amount of from 5.5 to 15.0 weight percent based on the total weight of the polyglycerol and cyclic tetraglycerol in an amount of from 0.5 to 8.0 weight percent based on the total weight of the polyglycerol, ;
Wherein the pentaglycerol comprises a non-cyclic pentaglycerol in an amount of from 3.0 to 11.0 weight percent based on the total weight of the polyglycerol, and a cyclic pentaglycerol in an amount of from 0.5 to 8.0 weight percent based on the total weight of the polyglycerol ≪ / RTI > 3. The method of claim 2,
The diglycerol comprises non-cyclic diglycerol in an amount of from 6.0 to 15.0 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 5.0 to 13.0 wt% based on the total weight of the polyglycerol, ;
Triglycerol comprises non-cyclic triglycerol in an amount of 7.0 to 15.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 2.5 to 9.5 weight percent based on the total weight of the polyglycerol, ;
The tetraglycerol comprises cyclic tetraglycerol in an amount of from 5.0 to 13.0 wt.%, Based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 1.0 to 8.0 wt.%, Based on the total weight of the polyglycerol, ;
Wherein the pentaglycerol comprises a non-cyclic pentaglycerol in an amount of from 3.0 to 11.0 weight percent based on the total weight of the polyglycerol, and a cyclic pentaglycerol in an amount of from 0.5 to 8.0 weight percent based on the total weight of the polyglycerol ≪ / RTI > 5. The polyglycerol composition according to any one of claims 1 to 4, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is
Diglycerol in an amount of 15.0 to 23.5% by weight, based on the total weight of polyglycerol;
Triglycerol in an amount of from 13.5 to 20.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 10.0 to 17.0 wt% based on the total weight of polyglycerol;
Pentaglycerol in an amount of from 8.0 to 14.5% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 8.0 to 11.5% by weight, based on the total weight of polyglycerol;
Heptaglycerol in an amount of 7.5-11.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of 6.5 to 10.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of 4.0 to 8.0 wt% based on the total weight of polyglycerol;
Decaglycerol in an amount of from 1.5 to 6.0% by weight, based on the total weight of polyglycerol; And
0.5 to 5.0% by weight, based on the total weight of polyglycerol, of undecaglycerol
≪ / RTI > 6. The method of claim 5,
The diglycerol comprises non-cyclic diglycerol in an amount of from 8.0 to 12.5 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of from 7.5 to 11.0 wt% based on the total weight of the polyglycerol, ;
Triglycerol comprises cyclic triglycerol in an amount of from 9.0 to 13.0 weight percent based on the total weight of the polyglycerol and cyclic triglycerol in an amount of from 4.5 to 7.5 weight percent based on the total weight of the polyglycerol, ;
Tetraglycerol comprises cyclic tetraglycerol in an amount of from 7.5 to 11.0 weight percent based on the total weight of the polyglycerol and cyclic tetraglycerol in an amount of from 2.5 to 6.0 weight percent based on the total weight of the polyglycerol, ;
Wherein the pentaglycerol comprises a non-cyclic pentaglycerol in an amount of from 5.0 to 9.0 weight percent based on the total weight of the polyglycerol, and a cyclic pentaglycerol in an amount of from 2.5 to 6.0 weight percent based on the total weight of the polyglycerol ≪ / RTI > 7. Polyglycerol composition according to any one of claims 1 to 6, used for forming polyglycerol esters of fatty acids,
Diglycerol in an amount of 17.6 to 21.0% by weight, based on the total weight of polyglycerol;
Triglycerol in an amount of from 15.9 to 18.1% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of from 12.5 to 14.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 10.5 to 12.2 wt% based on the total weight of polyglycerol;
Hexaglycerol in an amount of 9.3 to 10.1% by weight, based on the total weight of polyglycerol;
Heptaglycerol in an amount of from 8.6 to 9.9% by weight, based on the total weight of polyglycerol;
Octaglycerol in an amount of 7.3 to 8.9% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of 5.5 to 6.4% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 2.9 to 4.5% by weight, based on the total weight of polyglycerol; And
Based on the total weight of the polyglycerol, 1.8 to 3.7% by weight undecaglycerol
≪ / RTI > 8. The method of claim 7,
The diglycerol comprises non-cyclic diglycerol in an amount of 9.1 to 11.4 wt% based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 8.5 to 9.5 wt% based on the total weight of the polyglycerol, ;
Triglycerol comprises non-cyclic triglycerol in an amount of 10.0 to 11.8 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of 5.9 to 6.3 weight percent based on the total weight of the polyglycerol, ;
Tetraglycerol comprises cyclic tetraglycerols in an amount of from 8.4 to 9.5% by weight, based on the total weight of the polyglycerols, and cyclic tetraglycerol in an amount of from 4.1 to 4.4% by weight, based on the total weight of the polyglycerols, ;
Wherein the pentaglycerol comprises cyclic pentaglycerol in an amount of from 6.7 to 7.6 weight percent based on the total weight of the polyglycerol and from 3.8 to 4.6 weight percent of cyclic pentaglycerol based on the total weight of the polyglycerol, ≪ / RTI > The polyglycerol composition of claim 1, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid
The diglycerol comprises non-cyclic diglycerol in an amount of 9.0 to 24.5 weight percent based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 6.5 to 10.0 weight percent based on the total weight of the polyglycerol, ;
Triglycerol comprises cyclic triglycerol in an amount of from 9.0 to 20.5% by weight, based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of from 3.5 to 6.5% by weight, based on the total weight of the polyglycerol, ;
The tetraglycerol comprises non-cyclic tetraglycerols in an amount of from 8.0 to 13.5% by weight, based on the total weight of the polyglycerols, and cyclic tetraglycerol in an amount of from 2.0 to 4.5% by weight, based on the total weight of the polyglycerols, ;
Wherein the pentaglycerol comprises a non-cyclic pentaglycerol in an amount of 6.0 to 9.0 weight percent based on the total weight of the polyglycerol, and a cyclic pentaglycerol in an amount of 2.0 to 5.0 weight percent based on the total weight of the polyglycerol ≪ / RTI > The polyglycerol composition of claim 7, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid
The diglycerol comprises non-cyclic diglycerol in an amount of 20.0 to 26.0 weight percent based on the total weight of the polyglycerol, and cyclic diglycerol in an amount of 6.5 to 8.0 weight percent based on the total weight of the polyglycerol, ;
Triglycerol comprises cyclic triglycerol in an amount of from 18.0 to 21.0 weight percent based on the total weight of the polyglycerol, and cyclic triglycerol in an amount of from 2.5 to 5.0 weight percent based on the total weight of the polyglycerol, ;
Tetraglycerol comprises cyclic tetraglycerol in an amount of from 11.0 to 14.5 wt% based on the total weight of the polyglycerol, and cyclic tetraglycerol in an amount of from 1.5 to 4.0 wt% based on the total weight of the polyglycerol, ;
Wherein the pentaglycerol comprises a non-cyclic pentaglycerol in an amount of 6.5 to 9.5 weight percent based on the total weight of the polyglycerol, and a cyclic pentaglycerol in an amount of 1.5 to 4.0 weight percent based on the total weight of the polyglycerol ≪ / RTI > 11. The fuel composition according to any one of claims 1 to 10, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of from 880 to 1230 mg KOH / g. 12. The fuel composition according to claim 11, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of from 1130 to 1230 mg KOH / g. 12. The fuel composition according to claim 11, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of from 880 to 1060 mg KOH / g. 12. The fuel composition of claim 11, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a hydroxyl value of 950 to 990. 15. The fuel composition according to any one of claims 1 to 14, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index of 1.4855 to 1.4935 at 25 占 폚. 16. The fuel composition according to any one of claims 1 to 15, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index at 50 DEG C of from 1.4895 to 1.4925. 17. The fuel composition according to any one of claims 1 to 16, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid has a refractive index at 50 DEG C of from 1.4900 to 1.4920. 18. The fuel composition according to any one of claims 1 to 17, wherein the polyglycerol ester of the fatty acid has a viscosity of less than 700 mPa s at 20 占 폚. 19. The fuel composition according to any one of claims 1 to 18, wherein the polyglycerol ester of the fatty acid has a viscosity of less than 200 mPa s at 20 占 폚. 20. The fuel composition according to any one of claims 1 to 19, wherein the polyglycerol ester of the fatty acid is prepared by reacting polyglycerol and fatty acid triglyceride in a ratio of polyglycerol to fatty acid triglyceride of from 1: 1 to 1: 8. . 21. The fuel composition according to any one of claims 1 to 20, wherein (b) the polyglycerol ester of the fatty acid is present in an amount of up to 0.5% by weight, based on the total fuel composition. 22. The fuel composition according to any one of claims 1 to 21, wherein (b) the polyglycerol ester of the fatty acid is present in an amount of up to 0.25% by weight, based on the total fuel composition. 22. The fuel composition according to any one of claims 1 to 22, wherein (b) the polyglycerol ester of the fatty acid is present in an amount of up to 0.2% by weight, based on the total fuel composition. 24. The fuel composition according to any one of claims 1 to 23, wherein (b) the polyglycerol ester of the fatty acid is present in an amount of up to 0.1% by weight, based on the total fuel composition. 25. The fuel composition according to any one of claims 1 to 24, wherein the fuel is selected from diesel, heavy fuel oil, marine gas oil and kerosene. 26. The fuel composition of claim 25, wherein the fuel is a marine gas oil. 27. The fuel composition according to any one of claims 1 to 26, further comprising (c) water. 28. The fuel composition of claim 27, further comprising (c) water in an amount of 10 to 70 weight percent, based on total fuel composition. 28. The fuel composition of claim 27, further comprising (c) water in an amount of 30 to 60 weight percent, based on total fuel composition. 28. The fuel composition of claim 27, further comprising (c) water in an amount of from 33 to 50% by weight, based on the total fuel composition. (a) a fuel and (c) water, and (b) a polyglycerol ester of a fatty acid, wherein the polyglycerol composition used to form the polyglycerol ester of the fatty acid is
Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol;
Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;
Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And
0.0 > 7% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol
≪ / RTI > wherein the fuel and water comprise a mixture of the fuel and the water. The method of claim 31, characterized by the characteristics of any one of claims 2 to 30. The polyglycerol composition used to form polyglycerol esters of fatty acids
Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol;
Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;
Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And
0.0 > 7% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol
By weight of the polyglycerol ester of the fatty acid to improve the stability of the fuel and water-containing fuel composition. The polyglycerol ester of a fatty acid is used together with a guide for use in preparing a fuel composition as defined in any one of claims 1 to 30 wherein the polyglycerol ester used to form the polyglycerol ester of the fatty acid The composition
Diglycerol in an amount of 11.0 to 34.0 wt% based on the total weight of polyglycerol;
Triglycerol in an amount of 9.5 to 24.5% by weight, based on the total weight of polyglycerol;
Tetraglycerol in an amount of 6.0 to 21.0% by weight, based on the total weight of polyglycerol;
Pentaglycerol in an amount of 3.5 to 19.0% by weight, based on the total weight of polyglycerol;
Hexaglycerol in an amount of from 6.0 to 13.5% by weight, based on the total weight of polyglycerol;
Heptaglycerols in an amount of 5.0 to 13.0 wt% based on the total weight of polyglycerol;
Octaglycerol in an amount of from 3.0 to 12.0% by weight, based on the total weight of polyglycerol;
Nonaglycerol in an amount of from 1.5 to 10.0% by weight, based on the total weight of polyglycerol;
Decaglycerol in an amount of 0.0 to 8.0% by weight, based on the total weight of polyglycerol; And
0.0 > 7% < / RTI > by weight, based on the total weight of polyglycerol, of undecaglycerol
≪ / RTI > and mixtures thereof. A fuel composition as described above substantially in accordance with any one of the embodiments. Substantially as hereinbefore described with reference to any one of the embodiments. Use as substantially as hereinbefore described with reference to any one of the embodiments. A kit substantially as hereinbefore described with reference to any one of the embodiments.

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