Method for producing unsaturated decanals

Patent metadata

Field	Value
Publication number	US-11197491-B2
Application number	US-201616305969-A
Country	US
Kind code	B2
Filing date	Jun 2, 2016
Priority date	Jun 2, 2016
Publication date	Dec 14, 2021
Grant date	Dec 14, 2021

Abstract

The present invention relates to a flavour mixture containing 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal. This flavour mixture can be produced advantageously from arachidonic acid or oils containing esters thereof.

First claim

The invention claimed is:

1. A method for producing unsaturated decanals comprising:
a) air oxidizing an educt comprising arachidonic acid or arachidonic acid ester,
wherein the educt is with a solvent selected from triacetin, triethyl citrate, and a combination thereof, and the solvent is in an amount of ≥2-≤20 wt, %, relative to the educt,

b) decomposing a resulting peroxide by heating at a temperature of ≥100° C. to ≤200° C. for ≥0.5 h-≤5 h, and forming unsaturated decanals, and
c) concentrating the unsaturated decanals.

2. The method according to claim 1 further comprising:
d) repeating a) to c) in that order.

3. The method according to claim 1 , wherein a) comprises gassing with air at an air volume ≥10-≤1000 l/h per kg.

4. The method according to claim 1 , wherein a) is carried out at a temperature of ≥100° C. and ≤200° C.

5. The method according to claim 1 , wherein a) is carried out for a period of ≥1 h to ≤20 h.

6. The method according to claim 1 , wherein c) comprises a fractional distillation.

7. The method according to claim 2 , wherein a) comprises gassing with air at an air volume ≥10-≤1000 l/h per kg.

8. The method according to claim 7 , wherein a) is carried out at a temperature of ≥100° C. and ≤200° C.

9. The method according to claim 8 , wherein a) is carried out for a period of ≥1 h to ≤20 h.

10. The method according to claim 1 , wherein the unsaturated decanals are chosen from 2E,4Z,7Z-tridecatrienal, 2E,4E,7Z-tridecatrienal, and 2E,4E-decadienal.

11. The method according to claim 10 further comprising:
d) repeating a) to c) in that order.

Assignees

• Symrise Ag

Inventors

• Ongouta Jekaterina
• Backes Michael
• Ley Jakob Peter
• Koppe Volkmar
• Koch Jens

Classifications

• C07C45/54

  of compounds containing doubly bound oxygen atoms, e.g. esters · CPC title

• A23L27/26

  Meat flavours · CPC title

• C07C45/53 Primary

  of hydroperoxides · CPC title

• A23L23/00

  Soups; Sauces (soya sauce A23L27/50; salad dressings, mayonnaise or ketchup A23L27/60); Preparation or treatment thereof · CPC title

• A23L19/18

  Roasted or fried products, e.g. snacks or chips · CPC title