Method for preparing organic peroxides

Patent metadata

Field	Value
Publication number	US-9758479-B2
Application number	US-201414910937-A
Country	US
Kind code	B2
Filing date	Jul 9, 2014
Priority date	Aug 8, 2013
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

A method for preparing peroxide, including a step of treating, in a reaction medium, a component having at least one tertiary alcohol grouping with a compound having at least one tertiary hydroperoxide function in the presence of a catalyst, said method being characterized in that the catalyst includes a sulphonic acid and a inorganic acid, the molar ratio between the sulphonic acid and the aforementioned component including at least one tertiary alcohol grouping ranges from 0.05 to 0.8, and the molar ratio between the inorganic acid and the aforementioned component including at least one tertiary alcohol grouping ranges from 0.05 to 0.8. Also, to the peroxide resulting directly from said preparation method.

First claim

The invention claimed is:

1. A process for preparing peroxide, comprising a step of placing in contact in a reaction medium a component containing at least one tertiary alcohol group with a compound containing at least one tertiary hydroperoxide function in the presence of a catalyst, wherein:
the catalyst comprises a sulfonic acid and a mineral acid,
the mole ratio between the sulfonic acid and said component comprising at least one tertiary alcohol group is between 0.05 and 0.8, and
the mole ratio between the mineral acid and said component comprising at least one tertiary alcohol group is between 0.05 and 0.8.

2. The process as claimed in claim 1 , wherein the mole ratio between the sulfonic acid and the component comprising at least one tertiary alcohol group is between 0.1 and 0.6.

3. The process as claimed in claim 1 wherein the mole ratio between the mineral acid and the component comprising at least one tertiary alcohol group is between 0.1 and 0.6.

4. The process as claimed in claim 1 , wherein the process is performed at atmospheric pressure (±0.2 bar).

5. The process as claimed in claim 1 , wherein said component and/or said compound comprises one or more aromatic functions such that the peroxide comprises at least one aromatic function.

6. The process as claimed in claim 1 , wherein said compound comprising a hydroperoxide group is selected from the group consisting of tert-butyl hydroperoxide, tert-amyl hydroperoxide, 1-methylcyclohexyl hydroperoxide and 1-methylcyclopentyl hydroperoxide.

7. The process as claimed in claim 1 , wherein said compound comprising a hydroperoxide group is selected from the group consisting of 2,5-dimethyl-2,5-dihydroperoxy-3-hexyne and 2,5-dimethyl-2,5-dihydroperoxyhexane.

8. The process as claimed in claim 1 , wherein said component comprising an alcohol group is selected from the group consisting of tert-butanol, tert-amyl alcohol, cumyl alcohol, 1-methylcyclohexanol and 1-methylcyclopentanol.

9. The process as claimed in claim 1 , wherein said component comprising an alcohol group is selected from the group consisting of α,α′-dihydroxydiisopropylbenzene, 2,5-dimethyl-2,5-dihydroxy-3-hexyne and 2,5-dimethyl-2,5-dihydroxyhexane.

10. The process as claimed in claim 1 , wherein the sulfonic acid is selected from the group consisting of alkyl sulfonic acid, aryl sulfonic acid, and mixtures thereof.

11. The process as claimed in claim 1 , wherein the mineral acid is selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid and perchloric acid, and mixtures thereof.

12. The process as claimed in claim 1 , wherein the stoichiometric excess between the reagents, namely between said compound comprising at least one tertiary hydroperoxide group and said compound containing at least one tertiary alcohol function, is between 0.01 and 1.

13. The process as claimed in claim 1 , wherein the step of placing in contact is performed at a temperature of between 10° C. and 60° C.

14. The process as claimed in claim 1 , wherein it comprises a step prior to said step of placing in contact in the reaction medium, consisting of a step of mixing the mineral acid with the sulfonic acid outside said reaction medium.

15. The process as claimed in claim 1 , wherein the catalyst consists solely of the sulfonic acid and the mineral acid.

Assignees

• Arkema France

Inventors

• Maj Philippe
• Hub Serge

Classifications

• B01J27/053

  Sulfates · CPC title

• B01J31/0225

  comprising sulfonic acid groups or the corresponding salts · CPC title

• C07C409/16 Primary

  the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides · CPC title

• C07C407/00 Primary

  Preparation of peroxy compounds · CPC title

• C07C407/003

  Separation; Purification; Stabilisation; Use of additives · CPC title