Method for purifying alkyl hydroperoxide by extraction with water and separation of the aqueous phase

Patent metadata

Field	Value
Publication number	US-12410125-B2
Application number	US-201917417427-A
Country	US
Kind code	B2
Filing date	Dec 20, 2019
Priority date	Dec 26, 2018
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

The present invention relates to a method for purifying a mixture containing at least one alkyl hydroperoxide, preferably tert-butyl hydroperoxide or tert-amyl hydroperoxide, and at least one corresponding dialkyl hydroperoxide, said method comprising at least one step of extraction with water and at least one separation step which is carried out within the aqueous phase, obtained following the extraction step, in order to recover an aqueous solution which is rich in alkyl hydroperoxide. The invention also relates to an aqueous composition which is rich in alkyl hydroperoxide and contains at least 0.1% by weight of dialkyl peroxide in relation to the total weight of the composition.

First claim

The invention claimed is:

1. A process for the purification of a mixture containing at least one alkyl hydroperoxide and at least one dialkyl peroxide, wherein it successively comprises:
a) at least one stage of extraction, carried out with water, of said mixture so as to obtain a first phase rich in alkyl hydroperoxide and a second phase rich in dialkyl peroxide, wherein the extraction stage a) is carried out with a water content which is at least 5 times greater than a content by weight of the mixture,
b) at least one stage of concentration of the first phase obtained in stage a) so as to obtain two new phases, known as third and fourth phase,
c) optionally a stage of separation by settling of the third phase so as to obtain a fifth and sixth phase,
d) optionally a stage of recovery of the fifth phase obtained in stage c).

2. The process as claimed in claim 1 , wherein the concentration stage b) is carried out starting from a process employing at least one semipermeable membrane or from a distillation process.

3. The process as claimed in claim 1 , further comprising stage c), a stage of separation by settling of the third phase so as to obtain a fifth and sixth phase, wherein the concentration stage b) is carried out in order to obtain a fifth phase containing at least 60% by weight of alkyl hydroperoxide and less than 0.1% by weight of dialkyl peroxide and the fourth phase is a solution containing less than 6% by weight of alkyl hydroperoxide, the proportions being calculated with respect to the total weight of the solution as defined in claim 1 .

4. The process as claimed in claim 3 , wherein the solution containing less than 6% by weight of alkyl hydroperoxide is recycled to the extraction stage a).

5. The process as claimed in claim 1 , wherein the concentration stage b) is a distillation carried out at a temperature of between 25° C. and 60° C.

6. The process as claimed in claim 1 , wherein the concentration stage b) is a distillation carried out at a pressure of between 5 and 300 mbar (millibars).

7. The process as claimed in claim 1 , wherein the alkyl hydroperoxide corresponds to the following general formula R 1 —OO—H in which R 1 represents:
a linear or branched C 4 -C 10 alkyl group optionally substituted by one or more hydroxyl groups or
a cyclic group comprising from 5 to 8 carbon atoms which is optionally aromatic and which is optionally substituted by one or more C 1 -C 3 alkyl groups.

8. The process as claimed in claim 1 , wherein R 1 represents a cyclic group comprising from 5 to 8 carbon atoms which is optionally aromatic or a branched C 4 -C 10 .

9. The process as claimed in claim 1 , wherein the alkyl hydroperoxide is selected from the group consisting of tert-butyl hydroperoxide, tert-amyl hydroperoxide, hexylene glycol hydroperoxide, tert-octyl hydroperoxide, tert-hexyl hydroperoxide, methylcyclopentyl hydroperoxide and methylcyclohexyl hydroperoxide.

10. The process as claimed in claim 1 , wherein the alkyl hydroperoxide is selected from the group consisting of tert-butyl hydroperoxide (TBHP) and tert-amyl hydroperoxide (TAHP).

11. The process as claimed in claim 1 , wherein the dialkyl peroxide corresponds to the following general formula R 2 —OO—R 3 in which R 2 and R 3 , which are identical or different, represent:
a linear or branched C 4 -C 10 alkyl group optionally substituted by one or more hydroxyl groups, or
a cyclic group comprising from 5 to 8 carbon atoms which is optionally aromatic and which is optionally substituted by one or more C 1 -C 3 alkyl groups.

12. The process as claimed in claim 1 , wherein R 2 and R 3 , which are identical or different, represent a branched C 4 -C 10 alkyl group optionally substituted by one or more hydroxyl groups.

13. The process as claimed in claim 1 , wherein the dialkyl peroxide is selected from the group consisting of di(tert-butyl) peroxide, di(tert-amyl) peroxide, di(3-hydroxy-1,1-dimethylbutyl) peroxide, di(tert-octyl) peroxide, di(tert-hexyl) peroxide, di(methylcyclopentyl) peroxide and di(methylcyclohexyl) peroxide.

14. The process as claimed in claim 1 , wherein the dialkyl peroxide is selected from the group consisting of di(tert-butyl) peroxide and di(tert-amyl) peroxide.

15. The process as claimed in claim 1 , wherein the alkyl hydroperoxide and the dialkyl peroxide exhibit identical R 1 , R 2 and R 3 groups.

16. The process as claimed in claim 1 , in which the hydroperoxide is prepared in an acidic medium.

Assignees

• Arkema France

Inventors

• Maj Philippe
• Blum Albert
• Hub Serge
• Van Hemelryck Bruno

Classifications

• C08K5/14

  Peroxides · CPC title

• B01D11/0492

  Applications, solvents used · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title

• C07C407/003 Primary

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