# US 2009/0260280 A1 · Method of formulating a fuel composition for use in internal-combustion engines

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2009/0260280 A1
- Document ID: US20090260280A1
- Status: Published application
- Kind: A1
- Application number: 12/105,164
- Filed: 2008-04-17
- Published: 2009-10-22
- Earliest claimed: 2008-04-17
- Inventors: William H. Klausmeier
- Web page: https://patentgrep.com/patent/US20090260280A1

## CPC

- C10L 1/328: {Oil emulsions containing water or any other hydrophilic phase}
- Y02E 50/10: Biofuels, e.g. bio-diesel
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A method of formulating a fuel composition for use in internal-combustion engines includes the step of providing a fuel. In addition, there is the step of forming the fuel composition by adding to the fuel a polar fluid and an emulsifier. The emulsifier is present in an amount effective for the biodiesel fuel, alcohol, water, and emulsifier to form an emulsion. The emulsifier includes an active surfactant mixture of oleic acid and ammonium oleate, wherein the ratio of oleic acid to ammonium oleate is no more than 60:40.

## Claims

### Claim 1

A method of formulating a fuel composition for use in internal-combustion engines, the method comprising:
providing a fuel; and
forming the fuel composition by adding to the fuel a polar fluid and an emulsifier, the emulsifier being present in an amount effective for the biodiesel fuel, alcohol, water, and emulsifier to form an emulsion, and wherein the emulsifier includes an active surfactant mixture of oleic acid and ammonium oleate, wherein the ratio of oleic acid to ammonium oleate is no more than 60:40.

### Claim 2 (depends on 1)

The method of claim 1, further comprising mixing the fuel composition with air to form an aerosol.

### Claim 3 (depends on 2)

The method of claim 2, further comprising combusting the fuel composition.

### Claim 4 (depends on 1)

The method of claim 1, further comprising requiring the emulsifier to include purified glyceryl monooleate.

### Claim 5 (depends on 1)

The method of claim 1, further comprising requiring the ration of active surfactant mixture of oleic acid and ammonium oleate to be substantially 50:50.

### Claim 6

A method involving forming a polyol fatty acid ester, the method comprising:
providing a polyol having at least three reactive alcohol groups;
selecting a fatty acid;
protecting all but a preselected one of the reactive alcohol groups on the polyol by reacting all but the preselected one of the reactive alcohol groups with protecting groups, wherein a single protecting group may protect one or more reactive alcohol groups;
linking the fatty acid to the polyol through an ester linkage by reacting the fatty acid with the preselected one of the reactive alcohol groups; and
forming the polyol fatty acid ester by removing the protecting groups;
wherein each of the steps is performed under conditions that would tend not to substantially reduce an unsaturated fatty acid.

### Claim 7 (depends on 6)

The method of claim 6, wherein the fatty acid is unsaturated.

### Claim 8 (depends on 6)

The method of claim 6, wherein the fatty acid is selected from the group consisting of arachidic, elaidic acid, erucic acid, gadoleic acid, margaroleic acid, myristoleic acid, linoleic acid, linolenic acid, palmitoleic acid and oleic acid.

### Claim 9 (depends on 6)

The method of claim 6, wherein the polyol is a noncyclic polyol.

### Claim 10 (depends on 6)

The method of claim 6, wherein the polyol is glycerol.

### Claim 11 (depends on 6)

The method of claim 6, wherein the protecting group is acetone.

### Claim 12 (depends on 6)

The method of claim 6, wherein the protecting group is benzaldehyde.

### Claim 13 (depends on 6)

The method of claim 6, wherein the step of removing the protecting group includes acid hydrolysis.

### Claim 14 (depends on 6)

The method of claim 6, wherein the step of removing the protecting group includes formation and subsequent hydrolysis of a borate ester.

### Claim 15 (depends on 13)

The method of claim 13, wherein the acid hydrolysis is performed using acetic acid.

### Claim 16 (depends on 6)

The method of claim 6, wherein each of the steps is performed under an inert atmosphere.

### Claim 17 (depends on 16)

The method of claim 16, wherein the inert atmosphere consists essentially of nitrogen.

### Claim 18 (depends on 6)

The method of claim 6, wherein each of the steps is performed in the same reaction vessel.

### Claim 19 (depends on 6)

The method of claim 6, further comprising purifying the fatty acid ester.

### Claim 20 (depends on 6)

The method of claim 6, further comprising combining the fatty acid ester with a hydrocarbon fuel and a polar fluid to form an emulsion suitable for use as a fuel composition in an internal-combustion engine.

### Claim 21 (depends on 6)

The method of claim 6, further comprising linking an additional moiety to a second reactive alcohol group different than the preselected one of the reactive alcohol groups.

### Claim 22 (depends on 21)

The method of claim 21, wherein the additional moiety nitrates one or both hydroxyl groups on the polyol fatty acid ester to produce a nitro polyol fatty acid ester.

### Claim 23 (depends on 22)

The method of claim 22, wherein the nitro polyol fatty acid ester is a cetane enhancer.

### Claim 24 (depends on 23)

The method of claim 23, wherein the cetane enhancer retains at least a portion of its surfactant properties.

### Claim 25 (depends on 21)

The method of claim 21, wherein the additional moiety is ammonia and the polyol fatty acid ester is glyceryl monooleate

### Claim 26

A method involving forming a polyol fatty acid ester, the method comprising:
providing a polyol having at least three reactive alcohol groups;
selecting a fatty acid chloride;
protecting all but a preselected one of the reactive alcohol groups on the polyol by reacting all but the preselected one of the reactive alcohol groups with protecting groups, wherein a single protecting group may protect one or more reactive alcohol groups;
linking the fatty acid chloride to the polyol through an ester linkage by reacting the fatty acid with the preselected one of the reactive alcohol groups in the presence of an acid scavenger; and
forming the polyol fatty acid ester by removing the protecting groups;
wherein each of the steps is performed under conditions that would tend not to substantially reduce an unsaturated fatty acid.

### Claim 27 (depends on 26)

The method of claim 26, wherein the acid scavenger is pyridine.

### Claim 28

A method involving separating monoglycerides from a mixture containing monoglycerides and multiglycerides, the method comprising:
providing a mixture of monoglycerides and multiglycerides;
selecting an extraction fluid having a nonpolar component and a polar component that includes aqueous ethanol;
preferentially associating the monoglycerides with the polar component and the multiglycerides with the nonpolar component by contacting the mixture with the extraction fluid; and
at least partially separating the monoglycerides from the multiglycerides by separating the polar component from the nonpolar component.

### Claim 29 (depends on 28)

The method of claim 28, wherein the monoglycerides and multiglycerides primarily include esters of oleic acid.

### Claim 30 (depends on 28)

The method of claim 28, wherein the polar component consists essentially of aqueous ethanol.

### Claim 31 (depends on 30)

The method of claim 30, wherein the aqueous ethanol includes about five percent water.

### Claim 32 (depends on 28)

The method of claim 28, wherein the nonpolar component includes hexane.

### Claim 33 (depends on 32)

The method of claim 32, wherein the polar component consists essentially of aqueous ethanol.

### Claim 34 (depends on 33)

The method of claim 33, wherein the extraction fluid includes about fifteen parts of the polar component for every ten parts of the nonpolar component.

### Claim 35 (depends on 28)

The method of claim 28, wherein the polar component is separated from the nonpolar component by contacting the two components with water.

### Claim 36 (depends on 28)

The method of claim 28, further comprising concentrating the polar component to concentrate the monoglycerides.

### Claim 37 (depends on 36)

The method of claim 36, further comprising combining the concentrated polar component with a hydrocarbon fuel and a polar fluid to form an emulsion suitable for use as a fuel composition in an internal-combustion engine.

### Claim 38 (depends on 37)

The method of claim 37, further comprising repeating the steps of preferentially associating the monoglycerides and separating the monoglycerides, using the ethanol component as the mixture.

### Claim 39 (depends on 38)

The method of claim 38, wherein the step of contacting the mixture with an extraction fluid includes using a counter-current process.

### Claim 40 (depends on 39)

The method of claim 39, wherein the counter-current process includes using the polar component in a descending phase and the nonpolar component in an ascending phase.

### Claim 41 (depends on 28)

The method of claim 28, further comprising using the monoglycerides as an emulsifier in a fuel composition for an internal-combustion engine.

### Claim 42 (depends on 28)

The method of claim 28, wherein the polar component and the nonpolar component form distinct phases.

### Claim 43

A method involving separating polyol monoesters from a mixture of polyol monoesters and polyol multi-esters, the polyol including at least a four-carbon chain, the method comprising:
providing a mixture of polyol monoesters and polyol multi-esters;
selecting an extraction fluid having a nonpolar component and a polar component;
preferentially associating the polyol monoesters with the polar component and the polyol multi-esters with the nonpolar component by contacting the mixture with the extraction fluid; and
at least partially separating the polyol monoesters from the polyol multi-esters by separating the polar component from the nonpolar component.