Purification of tocopherols

• US 4,617,406 A
• Filed: 02/11/1985
• Issued: 10/14/1986
• Est. Priority Date: 02/11/1985
• Status: Expired due to Term

• Current Assignee: Cognis Corporation (BASF SE)
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Willging, Stephen M.
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US06/700,416
• Time in Patent Office: 610 Days
• Field of Search: 549/413, 549/213
• US Class Current: 549/413
• 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

Tocopherol homologues found in a tocopherol-containing feed material can be purified by forming a borate tocopherol ester and then distilling the material containing the esterified tocopherol to remove the materials boiling at temperatures lower than the esterified tocopherol. The borate tocopherol esters remaining after distillation are then reacted with a member selected from the group consisting of: Water, methanol, and ethanol to form tocopherol homologues from the borate tocopherol ester, and the boron by product from this reaction is removed. The tocopherol is then recovered by collecting it, distilling it or by any other convenient collection method.

Claims

1. A process for the purification of tocopherol comprising:

(a) reacting the tocopherol in a tocopherol-containing feed material with a member selected from the group consisting of;

boric acid, an alkoxy boroxine, an alkoxy borate, a phenoxyboroxine, and a phenoxyborate to form a borate tocopherol ester;

(b) distilling the product of (a) to leave the borate tocopherol esters in the residue;

(c) releasing the tocopherol from the borate tocopherol ester left after distillation by reacting the borate tocopherol ester with a member selected from the group consisting of;

water, methanol and ethanol to form the tocopherol and a boron compound;

(d) removing the boron compound formed by the reaction of the water, methanol and ethanol in step (c), and then

(e) recovering the released tocopherol after step (d).

2. A process described in claim 1 wherein the reaction of step (a) is at a temperature in the range of from about 40°

to about 305°

C.

3. A process as described in claim 1 wherein an excess amount of water is used in step (c) to release the tocopherol, thereby forming boric acid.

4. A process as described in claim 1 wherein the tocopherol is released from the borate tocopherol ester by reacting it in step (c) with a member selected from the group consisting of:

Methanol and ethanol.

5. A process as described in claim 3 wherein the boric acid formed in step (c) is removed in step (d) by an aqueous phase separation.

6. A process as described in claim 4 wherein the boron compound formed in step (c) is removed by using an azeotropic distillation.

7. A process as described in claim 6 wherein the amount of methanol and ethanol used in step (c) is from about 3.5 to about 30 moles per mole of boron present.

8. A process as described in claim 7 wherein the tocopherol is recovered as a distillation product.