Aldehyde oxidation processes

Patent metadata

Field	Value
Publication number	US-9428435-B2
Application number	US-201414568667-A
Country	US
Kind code	B2
Filing date	Dec 12, 2014
Priority date	Dec 13, 2013
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

The oxidation of isobutyraldehyde produces isobutyric acid and byproducts, such as isopropyl formate. A process of reducing the isopropyl formate byproduct and other byproducts in the oxidation of isobutyraldehyde is described. The process uses a carbonyl compound, such as acetone, to reduce byproduct levels in the resulting product. Process for use of static mixers in oxidation reactions of aldehydes are also provided.

First claim

The invention claimed is:

1. A process of preparing isobutyric acid, comprising:
feeding an oxidant, a carbonyl compound and a feed composition comprising isobutyraldehyde to a reaction zone; and
withdrawing from the reaction zone a crude product composition comprising isobutyric acid and at least some of the carbonyl compound,

wherein the carbonyl compound is selected from C 3 -C 8 alkyl esters having no carbon chain exceeding four carbon atoms and C 3 -C 5 alkyl ketones, wherein the reaction zone has a residence time of less than 120 minutes, and wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise at least 7 weight percent of the carbonyl compound based on the total weight of the crude product composition,
wherein the feed composition comprises at least some of the carbonyl compound and wherein the feed composition is the result of combining at least two isobutyraldehyde compositions that each comprise isobutyraldehyde.

2. The process of claim 1 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 7 to 35 weight percent of the carbonyl compound based on the total weight of the crude product composition.

3. The process of claim 1 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 10 to 25 weight percent of the carbonyl compound based on the total weight of the crude product composition.

4. The process of claim 1 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 10 to 20 weight percent of the carbonyl compound based on the total weight of the crude product composition.

5. The process of claim 1 , wherein two or more feed compositions are fed separately to the reaction zone.

6. The process of claim 1 , further comprising feeding an isobutyric acid containing composition to the reaction zone.

7. The process of claim 1 , wherein the carbonyl compound and the feed composition are fed separately to the reaction zone.

8. The process of claim 1 , wherein the crude product composition comprises isobutyraldehyde and the method further comprises:
concentrating at least some of the carbonyl compound in the crude product composition and at least some of the isobutyraldehyde in the crude product composition into a recycle composition; and
concentrating at least some of the isobutyric acid in the crude product composition into an isobutyric acid product composition; and
feeding at least some of the recycle composition to the reaction zone,

wherein feeding at least some of the recycle composition to the reaction zone comprises combining at least some of the recycle composition into the feed composition before feeding the feed composition to the reaction zone.

9. The process of claim 1 , wherein the carbonyl compound is selected from C 3 -C 4 alkyl esters and C 3 -C 4 alkyl ketones.

10. The process of claim 1 , wherein the carbonyl compound is selected from methyl acetate, ethyl acetate, methyl ethyl ketone and acetone.

11. The process of claim 1 , wherein the carbonyl compound is ethyl acetate.

12. The process of claim 1 , wherein the carbonyl compound is acetone.

13. The process of claim 12 , wherein at least some of the acetone is obtained as a byproduct from an isobutyraldehyde oxidation reaction.

14. The process of claim 12 , at least some of the acetone is derived from the crude product composition.

15. The process of claim 1 , wherein the reaction zone comprises an oxidation catalyst.

16. The process of claim 1 , wherein the formation of the isopropyl formate is reduced by from 40% to 70% by weight compared with the production of isobutyric acid in the absence of the carbonyl compound.

17. The process of claim 1 , wherein the process is carried out at a temperature of 30 to 70° C. and pressure of 30 to 70 psig.

18. The process of claim 1 , wherein the reaction zone comprises a static mixer.

19. A process of preparing isobutyric acid, comprising:
feeding an oxidant, a carbonyl compound and a feed composition comprising isobutyraldehyde to a reaction zone;
withdrawing from the reaction zone a crude product composition comprising isobutyric acid and at least some of the carbonyl compound;
concentrating at least some of the carbonyl compound in the crude product composition and at least some of the isobutyraldehyde in the crude product composition into a recycle composition; and
concentrating at least some of the isobutyric acid in the crude product composition into an isobutyric acid product composition; and
feeding at least some of the recycle composition to the reaction zone,

wherein the carbonyl compound is selected from C 3 -C 8 alkyl esters having no carbon chain exceeding four carbon atoms and C 3 -C 5 alkyl ketones, and wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise at least 7 weight percent of the carbonyl compound based on the total weight of the crude product composition,
wherein the formation of the isopropyl formate is reduced by from 40% to 70% by weight compared with the production of isobutyric acid in the absence of the carbonyl compound.

20. The process of claim 19 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 7 to 35 weight percent of the carbonyl compound based on the total weight of the crude product composition.

21. The process of claim 19 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 10 to 25 weight percent of the carbonyl compound based on the total weight of the crude product composition.

22. The process of claim 19 , wherein the carbonyl compound is fed to the reaction zone in an amount sufficient to cause the crude product composition to comprise 10 to 20 weight percent of the carbonyl compound based on the total weight of the crude product composition.

23. The process of claim 19 , wherein the feed composition is the result of combining at least two isobutyraldehyde compositions that each comprise isobutyraldehyde.

24. The process of claim 19 , wherein two or more feed compositions are fed separately to the reaction zone.

25. The process of claim 19 , further comprising feeding an isobutyric acid containing composition to the reaction zone.

26. The process of claim 19 , wherein the feed composition comprises at least some of the carbonyl compound.

27. The process of claim 19 , wherein the carbonyl compound and the feed composition are fed separately to the reaction zone.

28. The process of claim 19 , wherein feeding at least some of the recycle composition to the reaction zone comprises combining at least some of the recycle composition into the feed composition before feeding the feed composition to the reaction zone.

29. The process of claim 19 , wherein the carbonyl compound is selected from C 3 -C 4 alkyl esters and C 3 -C 4 alkyl ketones.

30. The process of claim 19 , wherein the carbonyl compound is selected from methyl acetate, ethyl acetate, methyl ethyl ketone

Assignees

• Eastman Chem Co

Inventors

• Billodeaux Damon Ray
• Hampton Jr Kenneth Wayne
• Johnson Chad A

Classifications

• C07C67/44

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title

• C07C51/235 Primary

  of —CHO groups or primary alcohol groups · CPC title

• C07C51/16

  by oxidation (C07C51/145 takes precedence) · CPC title

• C07C53/124

  Acids containing four carbon atoms · CPC title