Cold flow additives

Patent metadata

Field	Value
Publication number	US-9315748-B2
Application number	US-201113081588-A
Country	US
Kind code	B2
Filing date	Apr 7, 2011
Priority date	Apr 7, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

This invention relates to a fuel composition, comprising: (A) a normally liquid fuel; and (B) a cold flow improving amount of (i) a metathesized natural oil; (ii) a metathesized natural oil derivative; or (iii) a mixture of (i) and (ii). The invention also relates to metathesized derivatives formed by the reaction of a metathesized natural oil with a nucleophile, oxidizer, aromatic compound, enophilic acid reagent, or a mixture of two or more thereof.

First claim

The invention claimed is:

1. A fuel composition, comprising:
(A) a normally liquid fuel, the normally liquid fuel comprising a middle distillate fuel; and
(B) a cold flow improving amount of (i) a metathesized natural oil, the metathesized natural oil comprising a metathesis oligomer and/or metathesis polymer; (ii) a metathesized natural oil derivative; or (iii) a mixture of (i) and (ii) for lowering the cloud point, pour point and/or cold filter plugging point of the normally liquid fuel.

2. The composition of claim 1 wherein (A) comprises a natural oil derived unsaturated carboxylic acid, salt and/or ester.

3. The composition of claim 1 wherein (A) is derived from petroleum or crude oil.

4. The composition of claim 1 wherein (A) is derived from a Fischer-Tropsch process.

5. The composition of claim 1 wherein (A) is derived from coal, natural gas, oil shale, biomass, or a mixture of two or more thereof.

6. The composition of claim 1 wherein (A) comprises a synthetic fuel.

7. The composition of claim 1 wherein (A) comprises kerosene, jet fuel, diesel fuel, fuel oil, heating oil, naphtha, or a mixture of two or more thereof.

8. The composition of claim 1 wherein (A) comprises one or more biofuels.

9. The composition of claim 1 wherein (A) comprises a mixture of a biofuel and a hydrocarbon fuel.

10. The composition of claim 1 wherein (A) comprises a biodiesel/bioalcohol blend, a biodiesel/petroleum middle distillate blend, or a mixture of two or more thereof.

11. The composition of claim 1 wherein (A) comprises a mixture of a natural oil-derived methyl ester and a petroleum middle distillate.

12. The composition of claim 1 wherein (A) has a sulfur content of up to about 0.05% by weight.

13. The composition of claim 1 wherein (A) has a 95% distillation point of up to about 370° C.

14. The composition of claim 1 wherein the metathesized natural oil is the product of a self-metathesis process or a cross-metathesis process.

15. The composition of claim 1 wherein the metathesized natural oil is made by reacting one or more natural oils and/or natural oil derived unsaturated carboxylic acids, salts and/or esters in the presence of a metathesis catalyst to form the metathesized natural oil.

16. The composition of claim 1 wherein the metathesized natural oil is made by reacting (a) one or more natural oils and/or natural oil derived unsaturated carboxylic acids, salts and/or esters with (b) another olefinic compound in the presence of a metathesis catalyst.

17. The composition of claim 15 wherein the natural oil derived unsaturated carboxylic acid, salt and/or ester comprises an unsaturated fatty acid with an alkene chain in the carboxylic acid portion of the molecule of from about 4 to about 30 carbon atoms, a terminal carboxylic acid group, and at least one carbon-carbon double bond in the alkene chain.

18. The composition of claim 15 wherein the natural oil derived unsaturated carboxylic acid, salt and/or ester comprises a metal salt of an unsaturated fatty acid with an alkene chain in the carboxylic acid portion of the molecule of from about 4 to about 30 carbon atoms, and at least one carbon-carbon double bond in the alkene chain, the metal being an alkali metal, an alkaline earth metal, a group IIIA metal, a group IVA metal, a group VA metal, a transition metal, a metal from the lanthanide series, a metal from the actinide series, or a mixture of two or more thereof.

19. The composition of claim 15 wherein the natural oil derived unsaturated carboxylic acid, salt and/or ester comprises an unsaturated fatty ester with an alkene chain in the carboxylic acid portion of the molecule of about 4 to about 30 carbon atoms, a terminal ester group, and at least one carbon-carbon double bond in the alkene chain.

20. The composition of claim 17 wherein the alkene chain in the carboxylic acid portion of the molecule contains one, two, three or four carbon-carbon double bonds.

21. The composition of claim 15 wherein the natural oil derived unsaturated carboxylic acid, salt and/or ester comprises a polyunsaturated fatty acid, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated fatty ester, or a mixture of two or more thereof.

22. The composition of claim 19 wherein the unsaturated fatty ester comprises an unsaturated monoester, an unsaturated polyol ester, or a mixture thereof.

23. The composition of claim 22 wherein the unsaturated polyol ester is derived from a polyol containing from 2 to about 10 carbon atoms, and from 2 to about 6 hydroxyl groups.

24. The composition of claim 19 wherein the unsaturated fatty ester comprises an unsaturated glyceride.

25. The composition of claim 24 wherein the unsaturated glyceride comprises an unsaturated monoglyceride, an unsaturated diglyceride, an unsaturated triglyceride, or a mixture of two or more thereof.

26. The composition of claim 15 wherein the natural oil derived unsaturated carboxylic acid, salt and/or ester comprises an unsaturated fatty acid, carboxylate salt of an unsaturated fatty acid and/or an unsaturated fatty ester with an alkene chain in the carboxylic acid portion of the molecule of about 10 to about 24 carbon atoms, and: a carbon-carbon double bond between the C 9 and C 10 carbon atoms in the alkene chain; or a carbon-carbon double bond between the C 6 and C 7 carbon atoms in the alkene chain; or a carbon-carbon double bond between the C 11 and C 12 carbon atoms in the alkene chain; or a carbon-carbon double bond between the C 13 and C 14 carbon atoms in the alkene chain; or carbon-carbon double bonds between the C 9 and C 10 carbon atoms and between the C 12 and C 13 carbon atoms in the alkene chain; or carbon-carbon double bonds between the C 9 and C 10 carbon atoms, between the C 12 and C 13 carbon atoms, and between C 16 and C 16 carbon atoms in the alkene chain; or carbon-carbon double bonds between the C 6 and C 7 carbon atoms, between the C 9 and C 10 carbon atoms, between the C 12 and C 13 carbon atoms, and between the C 15 and C 16 carbon atoms in the alkene chain.

27. The composition of claim 15 wherein the natural oil comprises vegetable oil, algae oil, fungus oil, animal oil or fat, tall oil, or a mixture of two or more thereof.

28. The composition of claim 15 wherein the natural oil comprises canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower seed oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camellina oil, pennycress oil, castor oil, coriander oil, almond oil, wheat germ oil, bone oil, lard, tallow, poultry fat, algal oil, yellow grease, fish oil, or a mixture of two or more thereof.

29. The composition of claim 15 wherein the natural oil comprises refined, bleached and/or deodorized natural oil.

30. The composition of claim 29 wherein the refined, bleached and/or deodorized natural oil comprises refined, bleached and/or deodorized soybean oil.

31. The composition of claim 15 wherein the natural oil or natural oil derived unsaturated carboxylic acid, salt and/or ester is partially hydrogenated prior to the reaction in the presence of the metathesis catalyst.

32. The composition of claim 1 wherein the metathesized natural oil comprises from 1

Assignees

• Dibiase Stephen A
• Rizvi Syed Q A
• Christensen S Alexander
• Elevance Renewable Sciences

Inventors

• Dibiase Stephen A
• Rizvi Syed Q A
• Christensen S Alexander

Classifications

• C10L1/1963

  mono-carboxylic · CPC title

• C10L1/191

  of di- or polyhydroxyalcohols · CPC title

• C10L1/19

  Esters {ester radical containing compounds; ester ethers; carbonic acid esters (C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence)} · CPC title

• C10L1/1915

  complex esters (at least 3 ester bonds) · CPC title

• C10L1/1973

  mono-carboxylic · CPC title