Method for producing fatty acid esters

• US 6,211,390 B1
• Filed: 12/03/1999
• Issued: 04/03/2001
• Est. Priority Date: 09/19/1996
• Status: Expired due to Fees

• Current Assignee: Peter Siegfried
• Original Assignee: Peter Siegfried
• Inventors: Weidner, Eckhard, Peter, Siegfried, Ganswindt, Ruth
• Primary Examiner(s): CARR, DEBORAH D
• Application Number:
  US09/269,090
• Time in Patent Office: 487 Days
• Field of Search: 554/170, 554/169
• US Class Current: 554/170
• CPC Class Codes: C07C 67/58 by liquid-liquid treatment
• CPC Class Codes: C07C 69/52 Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence

Abstract

The invention concerns a method for producing fatty acid esters from fatty acid triglyceride and in particular from animal or vegetable fats and oils by transesterification with a monovalent low-molecular weight alcohol in the presence of a homogeneous or heterogeneous catalyst. In accordance with the invention, the formed fatty acid ester is extracted from the reaction mixture by means of a near-critical extractant. In this way fatty acid esters are obtained at high yield and excellent purity. As the extractant preferably a low pressure gas having a reduced temperature at 20° C. of about 0.7, preferably of equal to or greater than 0.7, is employed. Preferred extractants are carbon dioxide, propane, butane, dimethyl ether, ethyl acetate or mixtures thereof.

Claims

1. A method for producing fatty acid esters comprising transesterification of fatty acid triglyceride with a monovalent alcohol of 1 to 6 carbon atoms in the presence of a homogeneous or heterogeneous catalyst in a reaction mixture, wherein said fatty acid esters are removed from said reaction mixture by extraction using a near-critical extractant, except for carbon dioxide under supercritical conditions.

2. The method according to claim 1 wherein said extractant is a gas having a reduced temperature at 20°

C. of about 0.7.

3. The method according to claim 1 wherein said extractant is a gas having a reduced temperature at 20°

C. of greater than about 0.7.

4. The method according to any one of claims 1 to 3 wherein said extractant is selected from the group consisting of carbon dioxide, propane, butane, dimethyl ether, ethyl acetate and a mixture of at least two of the foregoing.

5. The method according to claim 4 wherein said extractant is employed at a density which is at least equal to the critical density and at a temperature between about 0°

C. and about 200°

C.

6. The method according to claim 5 wherein said temperature is between about 30°

C. and about 100°

C.

7. The method according to claim 5 wherein propane or butane or dimethyl ether is employed as the extractant.

8. The method according to claim 1 wherein said monovalent alcohol has 1 to 4 carbon atoms.

9. The method according to claim 2 wherein said monovalent alcohol is methanol or ethanol.

10. The method according to claim 1 wherein said fatty acid triglyceride is selected from the group consisting of animal fats, animal oils, vegetable fats and vegetable oils.

11. The method of claim 10 wherein said fatty acid triglyceride has about 10 to about 22 carbon atoms in the fatty acid radical.

12. The method of claim 11 wherein said fatty acid triglyceride has about 12 to about 18 carbon atoms in the fatty acid radical.

13. The method according to claim 1 wherein an ion exchange resin is employed as the heterogeneous catalyst.

14. The method according to claim 13 wherein said ion exchange resin is a strongly alkaline ion exchange resin.

15. The method according to claim 1 wherein an alkali is employed as the homogeneous catalyst.

16. The method according to claim 1 wherein transesterification takes place at a temperature of about 20°

C. to about 100°

C.

17. The method according to claim 16 wherein transesterification takes place at a temperature of about 30°

C. to about 80°

C.

18. The method according to claim 17 wherein transesterification takes place at about 50°

C. to about 75°

C.

19. The method according to claim 1 wherein transesterification takes place at a pressure between ambient pressure and the vapor pressure of the monovalent alcohol.

20. The method according to claim 1 wherein said extraction is started after at least about 80% of the employed fatty acid triglyceride is converted to fatty acid ester.

21. The method according to claim 20 wherein extraction is started after about 80 to about 95% of the employed fatty acid triglyceride is converted to fatty acid ester.

22. The method according to claim 4 wherein extraction takes place in a countercurrent column to which the extractant is supplied in a lower region thereof and to which the reaction mixture to be extracted, comprising said fatty acid ester, is supplied to a middle region of the countercurrent column, and the extractant enriched with fatty acid ester and said monovalent alcohol is withdrawn at the top of the column, and glycerol substantially freed from fatty acid ester is withdrawn at the bottom of the column.

23. The method according to claim 22 wherein the extractant enriched with fatty acid ester and monovalent alcohol is freed from fatty acid ester in a rectifying column by reduced pressure, increased temperature, or the combination of reduced pressure and increased temperature, and fatty acid ester is withdrawn at the bottom and extractant enriched with monovalent alcohol is withdrawn at the top of the rectifying column.

24. The method according to claim 23 wherein the monovalent alcohol is separated from the extractant in a condenser.

25. The method according to claim 24 wherein the separated monovalent alcohol is supplied to said reaction mixture for further transesterification of said fatty acid triglyceride.

26. The method according to claim 24 wherein the extractant freed from alcohol is condensed in a condenser.

27. The method according to claim 26 wherein the extractant freed from alcohol and condensed in a condenser is recycled to the extraction column.