Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions

Patent metadata

Field	Value
Publication number	US-9422508-B2
Application number	US-201113293185-A
Country	US
Kind code	B2
Filing date	Nov 10, 2011
Priority date	Feb 3, 2006
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

Compositions containing phenolic antioxidant solutions are provided. The invention further provides methods of making and using such compositions as well as compositions that contain both biodiesel and at least one antioxidant concentrate solutions and blended fuel compositions containing biodiesel blended with other fuels.

First claim

What is claimed is:

1. A composition comprising:
a) at least about 22% by weight of at least one phenolic antioxidant;
b) at least about 0.5% by weight of at least one metal chelating compound; and
c) at least one solvent comprising at least one compound selected from glycols, glycol ethers, glycol ether ester compounds, C 1 -C 25 monofunctional alcohols, C 1 -C 25 esters, C 3 -C 14 ketones, C 2 -C 10 amides, C 2 -C 10 ethers, and nitro compounds,

wherein at least one phenolic antioxidant and at least one metal chelating compound are dissolved in the solvent, and the composition is readily miscible in biodiesel.

2. The composition of claim 1 , wherein the composition comprises at least about 25% by weight of at least one phenolic antioxidant.

3. The composition of claim 1 , wherein the composition Comprises from about 22% to about 40% by weight of a phenolic antioxidant and about 0.5% to about 10% by weight of a metal chelating compound.

4. The composition of claim 1 , wherein the at least one solvent is a single compound selected from monofunctional C 1 -C 25 alcohols, C 2 -C 10 amides, C 2 -C 10 ethers and glycol ethers.

5. The composition of claim 1 , wherein the at least one solvent is a single compound selected from C 1 -C 12 glycol ethers.

6. The composition of claim 1 , wherein the at least one solvent is a single compound selected from ethylene glycol monopropyl ether, diethylene glycol mono butyl ether, ethylene glycol mono 2-ethylhexyl ether, DMF, THF, propanol, and ethanol.

7. The composition of claim 1 , wherein the at least one solvent is a single compound selected from ethylene glycol monopropyl ether, diethylene glycol mono butyl ether and ethylene glycol mono 2-ethylhexyl ether.

8. The composition of claim 1 , wherein the at least one solvent comprises at least two compounds selected from glycols, glycol ethers, glycol ether ester compounds, C 1 -C 25 monofunctional alcohols, C 1 -C 25 esters, C 3 -C 14 ketones, C 2 -C 10 amides, C 2 -C 10 ethers, and nitro compounds.

9. The composition of claim 1 , wherein the at least one phenolic antioxidant is selected from diphenols, bisphenols and triphenols.

10. The composition of claim 1 , wherein the at least one phenolic antioxidant is selected from diphenols and triphenols.

11. The composition of claim 1 , wherein the at least one phenolic antioxidant is tert-butyl hydroquinone or t-butyl catechol.

12. The composition of claim 1 , wherein the at least one phenolic antioxidant is pyrogallol.

13. The composition of claim 1 , wherein the at least one phenolic antioxidant is tert-butyl hydroquinone, the at least one metal chelating compound is citric acid and the solvent comprises at least one C 1 -C 25 glycol ether, at least one C 1 -C 25 ester, and at least one glycol.

14. The composition of claim 1 , wherein the composition comprises zero to 10% by weight of total surface active agents.

15. The composition of claim 1 , wherein the composition comprises:
a) between about 22% and about 50% by weight of at least one phenolic antioxidant,
b) between about 1.0% and about 3.0% by weight of at least one metal chelating compound, and
c) between about 50% and about 77.5% by weight of a glycol ether selected from ethylene glycol monopropyl ether and diethylene glycol monobutyl ether.

16. A composition comprising:
a) from about 0.001 to about 5 weight % of an antioxidant composition, wherein the antioxidant composition is the composition of claim 1 , and
b) at least one fatty acid or ester of fatty acid.

17. The composition of claim 16 , wherein the at least one fatty acid or ester of fatty acids is biodiesel.

18. The composition of claim 16 wherein the composition comprises at least about 90% by weight of the at least one esters of fatty acids.

19. The composition of claim 17 , wherein the composition comprises from 0.001 to 0.4 weight % of the antioxidant composition.

20. A composition comprising:
a) at least one burnable fuel source, and
b) a biodiesel composition, wherein the biodiesei composition is the composition of claim 17 .

21. The composition of claim 20 , wherein the at least one burnable fuel source comprises at least one petroleum distillate.

22. The composition of claim 20 , wherein the at least one burnable fuel source comprises petroleum diesel.

23. The composition of claim 22 , wherein the composition comprises at least about 2% by weight of the biodiesel composition.

24. A method for increasing the oxidative stability of at least one fatty acid or ester of fatty acid, comprising combining the at least one fatty acid or ester of fatty acid with the composition of claim 1 .

25. The method of claim 24 , wherein at least one fatty acid or ester of fatty acids is biodiesel.

26. A composition comprising:
a) at least about 1.5% by weight of a phenolic antioxidant;
b) at least about 0.5% by weight of a metal chelating compound; and
c) at least one solvent comprising at least one compound selected from glycols, glycol ethers, glycol ether eater compounds, C 1 -C 25 monofunctional alcohols, C 1 -C 25 esters, C 3 -C 14 ketones, C 2 -C 10 amides, C 2 -C 10 ethers, and nitro compounds,

wherein the at least one phenolic antioxidant and the at least one metal chelating compound are dissolved in the at least one solvent, the composition comprises 0% to 10% by weight of total surface active agents, and the composition is readily miscible in biodiesel.

27. The composition of claim 26 , wherein the composition comprises 0% to 5% by weight of total surface active agents.

28. The composition of claim 26 , wherein the composition comprises from about 15% to about 40% by weight of at least one phenolic antioxidant and about 0.5% to about 10% by weight of at least one metal chelating compound.

29. The composition of claim 26 , wherein the at least one solvent is a single compound selected from monofunctional C 1 -C 25 alcohols, C 2 -C 10 amides, C 2 -C 10 ethers and glycol ethers.

30. The composition of claim 26 , wherein the at least one solvent is a single compound selected from C 1 -C 12 glycol ethers.

31. The composition Of claim 26 , Wherein the at least one solvent is a single compound selected from ethylene glycol monopropyl ether, diethylene glycol mono butyl ether, ethylene glycol mono 2-ethylhexyl ether, DMF, THF, propanol, and ethanol.

32. The composition of claim 26 , wherein the at least one solvent is a single compound selected from ethylene glycol monopropyi ether, diethylene glycol mono butyl ether and ethylene glycol mono 2-ethylhexyl ether.

33. The composition of claim 26 , wherein the at least one solvent comprises at least two compounds selected from glycols, glycol ethers, glycol ether ester compounds, C 1 -C 25 monofunctional alcohols, C 1 -C 25 esters, C 3 -C 14 ketones, C 2 -C 10 amides, C 2 -C 10 ethers, and nitro compounds.

34. The composition of claim 26 , wherein the at least one phenolic antioxidant is selected from diphenols, bisphenols and triphenols.

35. The composition of claim 26 , wherein the at least one phenolic antioxidant is selected from diphenols and triphenols.

36. The composition of claim 26 wherein the at least one phenolic. antioxidant is tert-butyl h

Assignees

• Carter Thomas Edward
• Laningham Joy Lynn
• Hudnall Phillip Montgomery
• Cline Sharon Metcalf
• Eastman Chem Co

Inventors

• Carter Thomas Edward
• Laningham Joy Lynn
• Hudnall Phillip Montgomery
• Cline Sharon Metcalf

Classifications

• C10L1/1824

  mono-hydroxy · CPC title

• C10L1/2222

  (cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates (C10L1/221 takes precedence) · CPC title

• C10L1/1852

  Ethers; Acetals; Ketals; Orthoesters · CPC title

• C10L1/1883

  polycarboxylic acid · CPC title

• C11B5/0021

  containing oxygen · CPC title