STABILIZED VEGETABLE OILS AND METHODS OF MAKING SAME

• US 20080262255A1
• Filed: 02/15/2008
• Published: 10/23/2008
• Est. Priority Date: 08/16/2006
• Status: Abandoned Application

• Current Assignee: Bunge Oils, Inc. (Bunge Limited)
• Original Assignee: Bunge Oils, Inc. (Bunge Limited)
• Inventors: Higgins, Neil Wallace, Stults, Jerry F.
• Application Number:
  US12/032,472
• Publication Number:
  US 20080262255A1
• Time in Patent Office: Days
• US Class Current: 554/223
• CPC Class Codes: C07D 307/28 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F

Abstract

A method for modifying ethylenic unsaturation in a triglyceride. One or more unsaturated fatty acyl moieties present in the triglyceride are substituted with a lactone or ketone moiety via a electron acceptor mediated reaction. The resulting reaction products are useful, for example, as lubricants, metalworking fluids, mold release agents, hydraulic fluids, or dielectric fluids, or as components of lubricants, metalworking fluids, mold release agents, hydraulic fluids, or dielectric fluids, and intermediates for polymer synthesis.

Claims

1. A triglyceride having the structure:

2. The triglyceride of claim 1 in which R¹, R², and R³ are independently palmitoleic acyl, stearic acyl, oleic acyl, linoleic acyl, or linolenic acyl.

3. A lubricant comprising the triglyceride of claim 1.

4. A hydraulic fluid comprising the triglyceride of claim 1.

5. A dielectric fluid comprising the triglyceride of claim 1.

5A. A. A metalworking fluid comprising the triglyceride of claim 1.

5B. B. A mold release agent comprising the triglyceride of claim 1.

6. A triglyceride having the structure:

7. The triglyceride of claim 6 in which R¹, R², and R³ are independently palmitoleic acyl, stearic acyl, oleic acyl, linoleic acyl, or linolenic acyl.

8. A lubricant comprising the triglyceride of claim 6.

9. A hydraulic fluid comprising the triglyceride of claim 6.

10. A dielectric fluid comprising the triglyceride of claim 6.

10A. A. A metalworking fluid comprising the triglyceride of claim 6.

10B. B. A mold release agent comprising the triglyceride of claim 6.

11. An intermediate for polymer synthesis comprising the hydrogenated triglyceride of claim 6.

12. An intermediate for polymer synthesis comprising the hydroxylated triglyceride of claim 6.

13. A method for modifying ethylenic unsaturation in a triglyceride, comprising:

providing a triglyceride having at least one fatty acyl moiety with a site of unsaturation, the triglyceride having the structure;

14. The method of claim 13, in which at least one of R¹, R₂, and R³ is palmitoleic acyl, oleic acyl, linoleic acyl, linolenic acyl, alpha-eleostearic acyl, ricinoleic acyl, gadoleic acyl, arachidonic acyl, cetoleic acyl, or erucic acyl.

15. The method of claim 13, in which R¹, R², and R³ are independently palmitoleic acyl, stearic acyl, oleic acyl, linoleic acyl, or linolenic acyl.

16. The method of claim 13, in which the triglyceride comprises soybean oil triglyceride, partially hydrogenated soybean oil triglyceride, canola oil triglyceride, high oleic canola oil triglyceride, cottonseed oil triglyceride, rapeseed oil triglyceride, palm oil triglyceride, triglyceride of palm oil fractions, corn oil triglycerides, triglycerides made from distilled tall oil, partially hydrogenated forms of any of the above oil triglycerides, or a combination of two or more of these.

17. The method of claim 13, in which the carboxylic acid comprises acetic acid, propanoic acid, butanoic acid, pentanoic acid, or hexanoic acid or a combination of two or more of these.

18. The method of claim 13, in which the carboxylic acid comprises acetic acid

19. The method of claim 13, in which the reaction is carried out in the presence of a metal ion.

20. The method of claim 13, in which the reaction is carried out in the presence of a metal ion comprising Mn, V, or Ce.

21. The method of claim 13, in which the reaction is carried out in the presence of Mn⁺³.

22. The method of claim 13, in which the reaction is carried out in the presence of manganese triacetate.

22A. A. The method of claim 13, in which the reaction is carried out in the presence of manganese (III) acetylacetonate.

23. The method of claim 13, in which the reaction is carried out in the presence of an electron acceptor.

24. A method for modifying ethylenic unsaturation in a triglyceride, comprising:

providing a triglyceride having at least one fatty acyl moiety with a site of unsaturation, the triglyceride having the structure;

25. The method of claim 24, in which at least one of R¹, R², and R³ is palmitoleic acyl, oleic acyl, linoleic acyl, linolenic acyl, alpha-eleostearic acyl, ricinoleic acyl, gadoleic acyl, arachidonic acyl, cetoleic acyl, or erucic acyl.

26. The method of claim 24, in which R¹, R², and R³ are independently palmitoleic acyl, stearic acyl, oleic acyl, linoleic acyl, or linolenic acyl.

27. The method of claim 24, in which the triglyceride comprises soybean oil triglyceride, canola oil triglyceride, high oleic canola oil triglyceride, cottonseed oil triglyceride, rapeseed oil triglyceride, palm oil triglyceride, triglyceride of palm oil fractions, corn oil triglycerides, triglycerides made from distilled tall oil, partially hydrogenated forms of any of the above oil triglycerides, or a combination of two or more of these.

28. The method of any of claims 24, in which the ketone comprises acetone, pentane-2,4-dione, benzophenone, cyclohexanone, diacetone alcohol, diisobutyl ketone, isophorone, methyl amyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isobutyl ketone, or a combination of two or more of these.

29. The method of claim 24, in which the ketone comprises acetone.

30. The method of claim 24, in which the reaction is carried out in the presence of a metal ion.

31. The method of claim 24, in which the reaction is carried out in the presence of a metal ion comprising Mn, V, or Ce.

32. The method of claim 24, in which the reaction is carried out in the presence of Mn⁺³.

33. The method of claim 24, in which the reaction is carried out in the presence of manganese triacetate.

33A. A. The method of claim 24, in which the reaction is carried out in the presence of manganese (III) acetylacetonate.

34. The method of claim 24, in which the reaction is carried out in the presence of an electron acceptor.

35. The method of claim 24, in which a carboxylate moiety is formed on at least one site of unsaturation.