Process for the production of diacyl peroxides

Patent metadata

Field	Value
Publication number	US-11976034-B2
Application number	US-202017596383-A
Country	US
Kind code	B2
Filing date	Jun 11, 2020
Priority date	Jun 12, 2019
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

Process for the production of a diacyl peroxide involving the reaction of an anhydride with an aldehyde and oxygen, removal of the formed carboxylic acid, production of an anhydride from said carboxylic acid, and recycling of the anhydride within the process.

First claim

What is claimed is:

1. Process for the production of a diacyl peroxide comprising the following steps:
a) producing a mixture comprising a diacyl peroxide and a carboxylic acid by reacting one or more anhydrides with the formula R 1 —C(═O)—O—C(═O)—R 2 with an aldehyde of the formula R 3 —C(═O)H and oxygen, wherein R 1 and R 3 are independently selected from linear and branched alkyl, cycloalkyl, aryl, and arylalkyl groups with 1 to about −17 carbon atoms, optionally substituted with oxygen- and/or halogen-containing substituents, and R 2 is selected from linear and branched alkyl, cycloalkyl, aryl, and arylalkyl groups with about 2 to about −17 carbon atoms, optionally substituted with oxygen- and/or halogen-containing substituents,
b) extracting or separating the carboxylic acid from the mixture in the form of its carboxylic acid salt or adduct,
c) liberating the carboxylic acid from the salt or adduct,
d) optionally producing an additional amount of carboxylic acid by reacting an aldehyde of the formula R 2 —C(═O)H with oxygen,
e) reacting the carboxylic acid obtained in step c) and optionally an additional amount of carboxylic acid of the formula R 2 —C(═O)OH—said additional amount of carboxylic acid being obtained from step d) and/or obtained in another way—with an acid anhydride or a ketene of the formula C(R 4 ) 2 =C=O, each R 4 being independently selected from H and CH 3 to form one or more anhydrides with the formula R 1 —C(═O)—O—C(═O)—R 2 , and
f) recycling at least part of the anhydride formed in step e) to step a).

2. Process according claim 1 wherein the carboxylic acid is reacted in step e) with acetic anhydride.

3. Process according to claim 1 wherein R 1 and each R 2 are identical.

4. Process according to claim 1 wherein an additional amount of carboxylic acid is produced in step d) and reacted in step e).

5. Process according to claim 1 wherein the carboxylic acid is extracted in step b) with an aqueous solution of a base to form a carboxylic acid salt and wherein the carboxylic acid is liberated from its salt in step c) by acidification of said extract.

6. Process according to claim 1 wherein the carboxylic acid is extracted in step b) with an aqueous solution of a base to form a carboxylic acid salt and wherein the carboxylic acid is liberated from its salt in step c) by electrodialysis.

7. Process according to claim 1 wherein, during step e), acetic acid is removed from the reaction mixture.

8. Process according to claim 1 wherein step e) is performed in a reactive distillation column.

9. Process according to claim 1 wherein the one or more anhydrides with the formula R 1 —C(═O)—O—C(═O)—R 2 is a symmetrical anhydride wherein R 1 and R 2 are selected from linear and branched alkyl, cycloalkyl, aryl, and arylalkyl groups with about 2 to about −17 carbon atoms, optionally substituted with oxygen- and/or halogen-containing substituents.

10. Process according to claim 1 wherein R 1 and each R 2 are independently selected from linear and branched alkyl groups with about 2 to about −8 carbon atoms.

11. Process according to claim 9 wherein the one or more anhydrides of the formula R 1 —C(═O)—O—C(═O)—R 2 are selected from the group of isobutyric anhydride, n-butyric anhydride, 2-methylbutyric anhydride, 3-methylbutyric anhydride, 2-methylhexanoic anhydride, 2-methylpentanoic anhydride, 2-propylheptanoic anhydride, n-nonanoic anhydride, isononanoic anhydride, cyclohexanecarboxylic anhydride, 2-ethylhexanoic anhydride, n-valeric anhydride, and isovaleric anhydride.

12. Process according to claim 1 wherein the aldehyde of the formula R 3 —C(═O)H is selected from the group of n-butanal, isobutanal, 2,2-dimethylpropanal, 3-methylbutanal, 2-methylbutanal, 2-methylpentanal, 2-ethylhexanal, n-heptanal, n-pentanal, isononanal, and 2-propylheptanal.

13. Process according to claim 3 wherein the diacyl peroxide is selected from the group of di-n-butyryl peroxide, di-2-methylbutyryl peroxide, di-3-methylbutyryl peroxide, di-isovaleryl peroxide, di-n-valeryl peroxide, di-2-methylpentanoyl peroxide, di-cyclohexylcarbonyl peroxide, di-n-nonanoyl peroxide, di-isononanoyl peroxide, and di-isobutyryl peroxide.

14. Process according to claim 1 wherein the diacyl peroxide is selected from the group of isononanoyl isobutanoyl peroxide, nonanoyl isobutanoyl peroxide, isobutanoyl heptanoyl peroxide, valeroyl 2-ethylhexanoyl peroxide, valeroyl 2-propylheptanoyl peroxide, valeroyl cyclohexylcarbonoyl peroxide, heptanoyl 3-methylbutanoyl peroxide, nonanoyl 3-methylbutanoyl peroxide, isononanoyl 3-methylbutanoyl peroxide, pentanoyl 3-methylbutanoyl peroxide, nonanoyl heptanoyl peroxide, isononanoyl heptanoyl peroxide, nonanoyl pentanoyl peroxide, isononanoyl pentanoyl peroxide, and isononanoyl nonanoyl peroxide.

15. Process according to claim 1 wherein step d) is performed in the same equipment as step a).

Assignees

• Nouryon Chemicals Int Bv

Inventors

• Tammer Martinus Catharinus

Classifications

• C07C407/003 Primary

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

• C07C51/083 Primary

  from carboxylic acid anhydrides · CPC title

• C07C407/00

  Preparation of peroxy compounds · CPC title

• C07C51/412

  by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part · CPC title

• C07C51/56

  from organic acids, their salts, their esters {or their halides, e.g. by carboxylation} · CPC title