IP Library Granted Patent US 11,421,109
Granted Patent B2
US 11,421,109 · App. 17/124,863 · Granted Aug 23, 2022

Enhanced alkyl ester containing oil compositions and methods of making and using the same

Inventors: Alexander T. McCurdy (Sioux Falls, SD); Matthew D. Reiners (Sioux Falls, SD); Bradley M. Heggeseth (Sioux Falls, SD); Bruce G. Pierson (Sioux Falls, SD); David D. Bushong (Sioux Falls, SD)
Assignee: Poet Research, Inc.
C08L91/00C08K5/101C08L95/00A23D9/013C08L2555/34C08L2555/64
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Quick Facts
Patent No.
US 11,421,109
App. No.
17/124,863
Granted
Aug 23, 2022
Kind
B2
Abstract

Vegetable oil compositions, as an example, corn oil, having an elevated lower alkyl ester content above about 7% weight percent of the total weight of the oil composition, and uses thereof are provided.

Claims (20)

1. A corn oil composition comprising corn oil with a fatty acid ethyl ester content greater than 7% w/w based on the total weight of the corn oil composition; a free fatty acid content including at least one fatty acid selected from the group consisting of C16 palmitic, C18 stearic, C18-1 oleic, C18-2 linoleic, and C18-3 linolenic; and an ion content of about 0.4 to about 20 ppm.

2. The corn oil composition of claim 1 , wherein the free fatty acid content is no greater than 5% w/w based on the total weight of the corn oil composition.

3. The corn oil composition of claim 1 , wherein the ion content includes alkali metal ions, alkaline metal ions, or combinations thereof.

4. The corn oil composition of claim 3 , wherein the ion content include metal ions selected from lithium, sodium, magnesium, potassium, calcium, or combinations thereof.

5. The corn oil composition of claim 4 , wherein the corn oil composition includes about 0.4 to about 10 ppm of the ion content.

6. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 23 to about 35% w/w of ethyl palmitate and about 10 to about 22% w/w of ethyl oleate.

7. The corn oil composition of claim 6 , wherein the fatty acid ethyl ester content includes about 40 to about 61% w/w of ethyl linoleate.

8. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 5 to about 22% w/w ethyl palmitate, about 1 to about 5% w/w ethyl stearate, about 23 to about 30% w/w ethyl oleate, about 53 to about 60% w/w ethyl linoleate, and about 1 to about 2% w/w ethyl linolenate.

9. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 23 to about 35% w/w ethyl palmitate, about 1 to about 5% w/w ethyl stearate, about 10 to about 22% w/w ethyl oleate, about 40 to about 61% w/w ethyl linoleate, and about 2 to about 3% w/w ethyl linolenate.

10. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 5 to about 35% w/w ethyl palmitate, about 1 to about 5% w/w ethyl stearate, about 10 to about 30% w/w ethyl oleate, about 40 to about 61% w/w ethyl linoleate, and about 1 to about 3% w/w ethyl linolenate.

11. The corn oil composition of claim 1 , wherein the corn oil composition has a fatty acid ethyl ester content up to about 80% w/w.

12. The corn oil composition of claim 1 , wherein the corn oil composition further includes an unsaponifiables content no greater than 3% w/w.

13. The corn oil composition of claim 1 , wherein the corn oil composition has a moisture content of no greater than 1% w/w.

14. The corn oil composition of claim 13 , wherein the corn oil composition has a moisture content of about 0.2% or greater.

15. The corn oil composition of claim 1 , wherein the corn oil composition has an insoluble content of no greater than 1.5% w/w.

16. The corn oil composition of claim 1 , wherein the corn oil is obtained from a fermentation residue of corn.

17. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content is greater than 18% w/w.

18. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes more polyunsaturated ethyl esters than monounsaturated ethyl esters and saturated ethyl esters.

19. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 54 to about 62 weight percent of polyunsaturated ethyl esters.

20. The corn oil composition of claim 1 , wherein the fatty acid ethyl ester content includes about 2.9 to about 4.2 times more polyunsaturated ethyl esters than monounsaturated ethyl esters.

Assignments (3)
SECURITY INTEREST Recorded Dec 22, 2021
From: POET RESEARCH, INC.
To: COBANK, ACB, AS ADMINISTRATIVE AGENT
Reel/Frame 058457/0123 →
SECURITY INTEREST Recorded Nov 29, 2021
From: POET RESEARCH, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 058231/0546 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2021
From: MCCURDY, ALEXANDER T.; REINERS, MATTHEW D.; HEGGESETH, BRADLEY M.; PIERSON, BRUCE G.; BUSHONG, DAVID D.
To: POET RESEARCH, INC.
Reel/Frame 057970/0667 →