Recovery of tocopherols

• US 5,646,311 A
• Filed: 05/28/1996
• Issued: 07/08/1997
• Est. Priority Date: 08/06/1993
• Status: Expired due to Fees

• Current Assignee: Cognis Corporation (BASF SE)
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Jordon, Volkmar, Gutsche, Bernhard, Johannisbauer, Wilhelm, Jeromin, Lutz, Hunt, Tracy K., Wogatzki, Herbert
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US08/654,483
• Time in Patent Office: 406 Days
• Field of Search: 549/413, 554/175
• US Class Current: 549/413
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 67/54 by distillation
• CPC Class Codes: C07C 69/24 esterified with monohydroxylic compounds
• 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: C07D 311/72 3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols

Abstract

Starting from a mixture containing tocopherol, fats and/or fat derivatives, more particularly fatty acids, and optionally sterol and/or sterol derivatives, the free fatty acids present in the mixture are esterified with an alcohol. The mixture is then transesterified with an alcohol in the presence of a basic catalyst. After the transesterification, the excess lower alcohol is distilled off from the reaction mixture. The transesterification catalyst and the glycerol present, if any, are removed and the fatty acid alkyl ester is distilled off from the mixture. Distillation of fatty acid alkyl esters can be accomplished with a packed column in sequence with a wiped film evaporator. The simultaneous recovery of tocopherol and sterol is possible. Tocopherols and sterols can be separated by the crystallization of sterols from a blend of organic solvents.

Claims

1. An evaporative process for the separation of fatty acid lower alkyl esters from a mixture additionally comprising tocopherols and sterols, said process comprising:

introducing said mixture into a moderately heated zone of elevated temperature and reduced pressure, said zone containing multiple packing elements in an essentially continuous bed, said elevated temperature and reduced pressure being effective to provide within said continuous bed a first vapor phase enriched with respect to said mixture in alkyl fatty acid esters and a first liquid phase enriched with respect to said mixture in tocopherols and sterols;

removing liquid phase enriched in tocopherols and sterols from said continuous bed at a point gravitationally below the point of introduction of said mixture into said heated zone;

removing vapor phase enriched in alkyl fatty acid esters from said continuous bed at a point gravitationally above the point of introduction of said mixture into said heated zone;

applying said liquid phase enriched in tocopherols and sterols as a film to a highly heated surface in proximity with a zone of reduced vapor pressure to provide a second vapor phase enriched with respect to said liquid phase in alkyl fatty acid esters and a second liquid phase enriched with respect to said first liquid phase in tocopherols and sterols as a film in contact with said heated surface;

removing said vapor enriched in alkyl fatty acid esters from said zone and removing said film of said second liquid phase from said heated surface, said removing of said film being accomplished by mechanical agitation; and

removing said second liquid phase from proximity with said zone of reduced vapor pressure to an environment of essentially ambient temperature.

2. A process of claim 1 wherein the mixture, prior to introduction into said packed column, is pre-heated and pre-distilled as a film from a continuous heated surface, said heated surface being at a temperature lower than said packed column, and wherein said film on said continuous surface is removed by gravity flow down said heated surface.

3. A process as claimed in claim 1 said mixture is introduced as a pre-heated liquid into essentially the mid-point of a packed column, the bottoms of the packed column are removed to a wiped film evaporator, and the bottoms from the wiped film evaporator are removed to a zone of ambient temperature.

4. A process as claimed in claim 3 wherein the vapor phase from the wiped film evaporator re-enters the packed column through the bottom of the column.

5. A process as claimed in claim 3 wherein the packed column is configured to provide 5 to 12 theoretical stages above the point of introduction of said mixture and 5 to 12 theoretical stages below the point of introduction of said mixture.

6. A process as claimed in claim 3 wherein the packed column is operated with a temperature and pressure at the top of the column of 120°

C. to 150°

C. and 0.1 mbar to 3 mbar and at the bottom of the column of 180°

C. to 220°

C. and 3 mbar to 9 mbar.

7. A process as claimed in claim 3 wherein said packed column is operated with a reflux ratio of 0.4 to 0.6.

8. A process as claimed in claim 3 wherein said packed column is operated with distillate as a percentage of feed of 60% to 80% by weight.

9. A process as claimed in claim 3 wherein the wiped film evaporator is operated with a temperature of 200°

C. to 300°

C. and pressure of 50 to 90 mbar.

10. A process as claimed in claim 1 wherein said second liquid phase contains less than 1% by weight of alkyl fatty acid esters.

11. A process for the separation of a portion of the alkyl fatty esters from a mixture additionally comprising tocopherols and sterols, said process comprising:

applying said mixture as a film to a heated surface in proximity with a zone of reduced vapor pressure to provide a vapor phase enriched with respect to said liquid phase in alkyl fatty acid esters, said vapor phase being essentially free of tocopherols and sterols, and a liquid phase enriched with respect to said first liquid phase in tocopherols and sterols as a film in contact with said heated surface;

removing said vapor enriched in alkyl fatty acid esters from said zone and removing said film of said liquid phase from said heated surface; and

removing said liquid phase from proximity with said zone of reduced vapor pressure to an environment of essentially ambient temperature, wherein said liquid phase is collected in an amount of from about 30% to about 60% by weight of said mixture.

12. A process as claimed in claim 11 wherein said removing of said film is accomplished by mechanical agitation.

13. A process as claimed in claim 11 wherein said applying and removing are accomplished by use of a falling film evaporator.

14. A process as claimed in claim 13 wherein said heated surface is at a temperature of from 100°

C. to 200°

C.

15. A process as claimed in claim 11 wherein said applying and removing are accomplished by use of a wiped film evaporator.

16. A process as claimed in claim 15 wherein said heated surface is at a temperature of from 150°

C. to 250°

C.

17. A process as claimed in claim 11 wherein the weight ratio of alkyl fatty esters to total weight of tocopherols and sterols combined in said mixture applied to said heated surface ranges from about 1.5:

1 to about 5;

1.

18. A process as claimed in claim 11 wherein said vapor enriched in alkyl fatty esters contains less than 5% by weight of tocopherols and sterols combined.