Modified vegetable oil lubricants

• US 9,359,572 B2
• Filed: 03/15/2010
• Issued: 06/07/2016
• Est. Priority Date: 03/13/2009
• Status: Active Grant

• Current Assignee: Battelle Memorial Institute
• Original Assignee: Battelle Memorial Institute
• Inventors: Benecke, Herman Paul, Garbark, Daniel B., Vijayendran, Bhima Rao, Cafmeyer, Jeffrey
• Primary Examiner(s): Oladapo, Taiwo
• Application Number:
  US13/256,094
• Publication Number:
  US 20120129746A1
• Time in Patent Office: 2,276 Days
• Field of Search: 508/459
• US Class Current: 1/1
• CPC Class Codes: C10M 105/42 Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
• CPC Class Codes: C10M 109/02 Reaction products
• CPC Class Codes: C10M 2207/301 used as base material
• CPC Class Codes: C10N 2030/02 Pour-point; Viscosity index
• CPC Class Codes: C10N 2030/08 Resistance to extreme temperature
• 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
• CPC Class Codes: C11C 3/04 by esterification of fats or fatty oils
• CPC Class Codes: C11C 3/10 Ester interchange

Abstract

Lubricants based on renewable feedstocks and methods of making them.

Claims

1. A method for producing a lubricant comprising:

forming a backbone modified diester of a biobased fatty acid by;

a) esterifying an epoxidized biobased fatty acid with a carboxylic acid anhydride to form the diester;

or

b) reacting an epoxidized biobased fatty acid with a carboxylic acid to form a beta ester alcohol, and reacting the beta ester alcohol with a second carboxylic acid, an acid anhydride, or an acid chloride to form the diester;

or

c) hydrolyzing an epoxidized biobased fatty acid to a diol and reacting the diol with a carboxylic acid, an acid anhydride, or an acid chloride to form the diester;

wherein the backbone modified diester of the biobased fatty acid is esterified with 2-butanol, 1,2-propylene glycol, 2-methyl-1,3-propane diol, 1,1,1-(trimethylol)propane, or neopentyl glycol;

the biobased fatty acid content being high oleic with an oleic content in a range of 70-85 wt %, mid oleic with an oleic content in a range of 40-70 wt %, an oleic content in a range of 85-95 wt %, a linoleic content in a range of 55-65 wt %, or a saturated fatty acid content in a range of 4-12 wt %;

wherein the esterified backbone modified diester of the biobased fatty acid has a viscosity of 4.57 to 24.74 cSt at 100°

C.

2. The method of claim 1 wherein the backbone modified diester incorporates an acid group selected from C₂-C₁₈ carboxylic acids.

3. The method of claim 2 wherein the acid group is acetic acid, propanoic acid, butyric acid, isobutyric acid, 2-ethylbutanoic acid, hexanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, or combinations thereof.

4. The method of claim 1 wherein the reaction takes place in the presence of a catalyst.

5. The method of claim 1 further comprising adding one or more functional components to the diester, the functional components selected from pour point depressants, anti-wear additives, diluent, extreme pressure additives, and antioxidants.

6. The method of claim 1 wherein a mixture of carboxylic acids are used.

7. A lubricant composition comprising a mixture of one or more of a backbone modified diester of a biobased fatty acid:

a) a diester product of a reaction of an epoxidized biobased fatty acid with a carboxylic acid anhydride;

or

b) a diester product of a reaction of a beta ester alcohol with a second carboxylic acid, an acid anhydride, or an acid chloride, the beta ester alcohol being the reaction product of an epoxidized biobased fatty acid with a first carboxylic acid;

or

c) a diester product of a reaction of a diol with a carboxylic acid, an acid anhydride, or an acid chloride, the diol being a hydrolyzed product of an epoxidized biobased fatty acid;

the backbone modified diester of the biobased fatty acid being esterified with 2-butanol, 1,2-propylene glycol, 2-methyl-1,3-propane diol, 1,1,1-(trimethylol)propane, or neopentyl glycol; and

the biobased fatty acid content being high oleic with an oleic content in a range of 70-85 wt %, mid oleic with an oleic content in a range of 40-70 wt %, an oleic content in a range of 85-95 wt %, a linoleic content in a range of 55-65 wt %, or a saturated fatty acid content in a range of 4-12 wt %;

wherein the esterified backbone modified diester of the biobased fatty acid has a viscosity of 4.57 to 24.74 cSt at 100°

C.

8. The lubricant composition of claim 7 wherein the backbone modified diester incorporates an acid group selected from C₂-C₁₈ carboxylic acids.

9. The lubricant composition of claim 8 wherein the acid group is acetic acid, propanoic acid, butyric acid, isobutyric acid, 2-ethylbutanoic acid, hexanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, or combinations thereof.

10. The lubricant composition of claim 7 wherein the lubricant composition has a pour point of less than about −

10°

C. in the absence of an added pour point depressant.

11. The lubricant composition of claim 7 further comprising one or more functional components selected from pour point depressants, anti-wear additives, diluent, extreme pressure additives, and antioxidants.

12. A lubricant composition comprising a mixture of one or more backbone modified diester of a biobased fatty acid having a formula:

13. The lubricant composition of claim 12 wherein the backbone modified diester incorporates an acid group selected from C₂-C₁₈ carboxylic acids.

14. The lubricant composition of claim 13 wherein the acid group is acid, propanoic acid, butyric acid, isobutyric acid, 2-ethylbutanoic acid, hexanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, or combinations thereof.

15. The lubricant composition of claim 12 wherein the lubricant composition has a pour point of less than about −

10°

C. in the absence of an added pour point depressant.

16. The lubricant composition of claim 12 further comprising one or more functional components selected from pour point depressants, anti-wear additives, diluent, extreme pressure additives, and antioxidants.