IP Library Granted Patent US 9,758,479
Granted Patent B2
US 9,758,479 · App. 14/910,937 · Granted Sep 12, 2017

Method for preparing organic peroxides

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Quick Facts
Patent No.
US 9,758,479
App. No.
14/910,937
Granted
Sep 12, 2017
Kind
B2
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.

Claims (18)

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.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2016
From: HUB, SERGE; MAJ, PHILIPPE
To: ARKEMA FRANCE
Reel/Frame 038513/0932 →