IP Library Granted Patent US 7,087,771
Granted Patent B2
US 7,087,771 · App. 10/953,327 · Granted Aug 8, 2006

Method of making alkyl esters using glycerin

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Quick Facts
Patent No.
US 7,087,771
App. No.
10/953,327
Granted
Aug 8, 2006
Kind
B2
Abstract

A method for making alkyl esters (e.g., methyl ester), such as biodiesel, from an oil source is described. The method involves converting the free fatty acids of the oil source into a mixture of mono-, di-, and tri-glycerides and subsequently transesterifying the newly formed glycerides as well as the originally present glycerides into fatty acid alkyl esters.

Claims (20)

1. A method of making an alkyl ester comprising the following steps:

providing an oil source, the oil source including free fatty acids or glycerides;

providing a glycerol source of at least 0.3 equivalents;

contacting the glycerol source and the oil source for a sufficient time for effective conversion of the free fatty acids and the glycerides into a mixture of mono-, di-, and tri-glycerides;

providing an alcohol in an excess between about 1.0 equivalents to about 10 equivalents;

reacting the mixture of glycerides with the alcohol for an effective conversion of the glycerides into fatty acid alkyl esters; and

recovering the fatty acid alkyl esters.

2. The method of claim 1 , wherein the alcohol is selected from the group consisting of methanol, ethanol, isopropanol, propanol, and butanol.

3. The method of claim 1 , wherein the alcohol is provided in an excess between about 1.0 equivalents to about 6.0 equivalents.

4. The method of claim 1 , wherein the alcohol is provided in an excess between about 1.0 equivalents to about 3.0 equivalents.

5. The method of claim 1 , wherein a vacuum is applied to reduce pressure over time during the step of contacting the glycerol source and the oil source.

6. The method of claim 5 , wherein the pressure is maintained at about 760 mmHg while heat is applied during the contacting step to reach reaction temperature, and the pressure is reduced over time after the reaction temperature has been reached.

7. The method of claim 5 , wherein the pressure is reduced over time from about 760 mmHg to less than about 100 mmHg.

8. The method of claim 6 , wherein the pressure is reduced over time from about 760 mmHg to less than about 100 mmHg.

9. The method of claim 6 , wherein the pressure is reduced over time from about 760 mmHg to between about 30 mmHg and about 60 mmHg.

10. The method of claim 6 , wherein the pressure is reduced over time from about 760 mmHg to less than about 30 mmHg.

11. The method of claim 6 , wherein the pressure is reduced over time from about 760 mmHg to less than about 10 mmHg.

12. The method of claim 5 , wherein the pressure is reduced over time and a constant stream of nitrogen is applied during the step of contacting the glycerol source and the oil source.

13. The method of claim 12 , wherein the constant stream of nitrogen is not applied until the pressure has been reduced to about 100 mmHg.

14. The method of claim 12 , wherein the constant stream of nitrogen is not applied until the pressure has been reduced to less than about 100 mmHg.

Assignments (9)
RELEASE OF SECURITY INTEREST Recorded Jul 1, 2022
From: UMB BANK, N.A., AS COLLATERAL TRUSTEE
To: REG SYNTHETIC FUELS, LLC; RENEWABLE ENERGY GROUP, INC.; REG SENECA, LLC; REG BIOFUELS, LLC
Reel/Frame 060562/0428 →
PATENT SECURITY AGREEMENT Recorded Jun 19, 2021
From: REG SENECA, LLC
To: UMB BANK, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 056628/0607 →
CHANGE OF NAME Recorded Sep 9, 2014
From: SENECA LANDLORD, LLC
To: REG SENECA, LLC
Reel/Frame 033705/0717 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Apr 28, 2011
From: STEPAN COMPANY
To: BIOSOURCE AMERICA, INCORPORATED
Reel/Frame 026257/0589 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2011
From: NOVA BIOSOURCE TECHNOLOGIES, LLC
To: SENECA LANDLORD, LLC
Reel/Frame 025597/0214 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2007
From: BIOSOURCE AMERICA, INC.
To: NOVA BIOSOURCE TECHNOLOGIES, LLC
Reel/Frame 019224/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2006
From: STEPAN COMPANY
To: BIOSOURCE AMERICA, INC.
Reel/Frame 017507/0412 →
SECURITY INTEREST Recorded Apr 7, 2006
From: STEPAN COMPANY
To: BIOSOURCE AMERICA, INC.
Reel/Frame 017456/0470 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2004
From: LUXEM, FRANZ J.; GALENTE, JENIFER HEYDINGER; TROY, WILLIAM M.; BERNHARDT, RANDALL J.
To: STEPAN COMPANY
Reel/Frame 015856/0113 →