Process for preparing 3-methylcyclopentadecane-1,5-dione

Patent metadata

Field	Value
Publication number	US-10053409-B2
Application number	US-201615578959-A
Country	US
Kind code	B2
Filing date	Jun 2, 2016
Priority date	Jun 3, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

The present invention relates to a process for producing 3-methylcyclopentadecane-1,5-dione of formula (I), which comprises the oxidation of 14-methyl-bicyclo[10.3.0]pentadecen[1 (12)] of formula (II) with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H 2 O 2 as sole oxidizing agent in the presence of water and where the amount of H 2 O 2 is at least 1.1 mol H 2 O 2 per mol of the compound of formula (II).

First claim

The invention claimed is:

1. A process for preparing 3-methylcyclopentadecane-1,5-dione, which comprises oxidizing 14-methylbicyclo[10.3.0]pentadecen[1(12)] with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H 2 O 2 as sole oxidizing agent in the presence of water and where the amount of H 2 O 2 is at least 1.1 mol H 2 O 2 per mol of 14-methylbicyclo[10.3.0]pentadecen[1(12)].

2. The process of claim 1 , wherein the amount of H 2 O 2 is from 1.4 to 4.0 mol H 2 O 2 per mol of 14-methylbicyclo[10.3.0]pentadecen[1(12)].

3. The process of claim 1 , wherein the amount of H 2 O 2 is from 1.5 to 3.5 mol H 2 O 2 per mol of 14-methylbicyclo[10.3.0]pentadecen[1(12)].

4. The process of claim 1 , wherein H 2 O 2 is added to the mixture of 14-methylbicyclo[10.3.0]pentadecen[1(12)] and formic acid.

5. The process of claim 3 , wherein the total amount of added H 2 O 2 is added over a period of at least 2 h.

6. The process of claim 3 , wherein the total amount of added H 2 O 2 is added over a period of from 2 to 24 h.

7. The process of claim 3 , wherein less than 70% of the total amount of H 2 O 2 used in the process is present at the beginning of the oxidation.

8. The process of claim 3 , wherein less than 70% and at most 50% of the total amount of H 2 O 2 used in the process is present at the beginning of the oxidation.

9. The process of claim 5 , wherein at least 50% of the total amount of H 2 O 2 are added to the reaction mixture while the oxidation reaction takes place.

10. The process of claim 1 , wherein the oxidation of the compound of 14-methylbicyclo[10.3.0]pentadecen[1(12)] is performed at a temperature of −20 to 100° C.

11. The process of claim 1 , wherein the oxidation of the compound of 14-methylbicyclo[10.3.0]pentadecen[1(12)] is performed at a temperature of from 0 to 80° C.

12. The process of claim 1 , wherein the oxidation of the compound of 14-methylbicyclo[10.3.0]pentadecen[1(12)] is performed at a temperature of from 10 to 60° C.

13. The process of claim 1 , wherein the concentration of water in the reaction mixture is from 3 to 25% by weight.

14. The process of claim 1 , wherein H 2 O 2 is used as an aqueous solution.

15. The process of claim 14 , wherein the concentration of H 2 O 2 in the aqueous H 2 O 2 is from 25 to 50% by weight.

16. The process of claim 1 , where the weight ratio of 14-methylbicyclo[10.3.0]pentadecen[1(12)] and the formic acid is in the range from 1:20 to 1:2.

Assignees

• Basf Se

Inventors

• Bru Roig Miriam
• Rüdenauer Stefan

Classifications

• C07C45/28 Primary

  of CHx-moieties · CPC title

• C07C45/27 Primary

  by oxidation (with ozone C07C45/40) · CPC title

• C07C2601/18

  with a ring being at least seven-membered · CPC title

• C07C49/385

  Saturated compounds containing a keto group being part of a ring · CPC title

• C01B15/01

  Hydrogen peroxide · CPC title