Method of making alkyl esters using glycerin

• US 6,822,105 B1
• Filed: 08/12/2003
• Issued: 11/23/2004
• Est. Priority Date: 08/12/2003
• Status: Expired due to Term

• Current Assignee: REG Seneca LLC (Chevron Corp.)
• Original Assignee: Stepan Company
• Inventors: Galante, Jenifer Heydinger, Bernhardt, Randall R., Luxem, Franz J., Troy, William M.
• Primary Examiner(s): Carr, Deborah D.
• Application Number:
  US10/639,048
• Time in Patent Office: 469 Days
• Field of Search: 554/156, 554/157
• US Class Current: 554/167
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/06 with glycerol
• CPC Class Codes: C11C 3/08 with fatty acids
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

A method for making alkylesters, or methylester specifically, 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

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

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

providing a glycerol source of at least 0.3 equivalent;

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

providing methanol in an excess between about 1.0 equivalents to about 3 equivalents;

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

recovering the fatty acid alkyl esters.

2. The method of claim 1 wherein the step of contacting the glycerol source and oil source is performed in the presence of a catalyst.

3. The method of claim 2 wherein the catalyst is selected from the group consisting of organotin compounds, organo titanium compounds, alkali acetates, earthalkali acetates, lewis acids, alkali carbonates, earthalkali carbonates, and combinations thereof.

4. The method of claim 3 wherein the catalyst is dibutyltin oxide.

5. The method of claim 3 wherein the catalyst is tetrabutyl titanate.

6. The method of claim 1 wherein the glycerol source is USP grade glycerol or purified glycerol.

7. The method of claim 1 wherein the glycerol source is crude glycerol recovered from a fat splitting or methanolysis of vegetable oil.

8. The method of claim 1 further comprising the step of

recovering the glycerol produced from the reaction of glycerides with the methanol;

and wherein the glycerol source includes at least in part the recycled glycerol without further purification.

9. The method of claim 1 wherein the step of contacting the glycerol source and oil source is performed at a temperature between about 140°

C. to 245°

C.

10. The method of claim 9 wherein the temperature is between about 160°

C. to 200°

C.

11. The method of claim 10 wherein the temperature is about 180°

C.

12. The method of claim 1 wherein the step of contacting the glycerol source and oil source is performed at a reduced pressure ranging from about 760 mmHg to 1 mmHg.

13. The method of claim 1 wherein the step of contacting the glycerol source and oil source is performed at a reduced pressure and under a constant stream of nitrogen.

14. The method of claim 1 wherein the step of contacting the glycerol source and oil source is performed under a constant stream of nitrogen.

15. The method of claim 1 wherein the method is performed in a batch process.

16. The method of claim 1 wherein the method is performed in a continuous process.

17. The method of claim 1 wherein the step of contacting the glycerol source and oil source is carried out to a residual acid value of below 5 (mgKOH/g).

18. The method of claim 17 wherein the step of contacting the glycerol source and oil source is carried out to a residual acid value of about 0.1 to about 1 (mgKOH/g).