Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols in the presence of a liquid phase

Patent metadata

Field	Value
Publication number	US-10532970-B2
Application number	US-201716307540-A
Country	US
Kind code	B2
Filing date	Jun 27, 2017
Priority date	Jun 29, 2016
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

Abstract

Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols where the oxidant is oxygen in the presence of a catalyst comprising platinum on a support in the presence of a liquid phase which contains at least 25 weight-% water based on the total weight of the liquid phase.

First claim

The invention claimed is:

1. A process for the preparation of alpha, beta unsaturated aldehydes of general formula (I)
(R 1 )(R 2 )C═C(R 3 )—CHO,  (I)

wherein R 1 , R 2 and R 3 , independently of one another, are selected from the group consisting of H, CH 3 and C 2 H 5 and wherein R 3 is H,
by oxidation of alcohols of general formula (II)
(R 1 )(R 2 )C═C(R 3 )—CH 2 —OH,  (II)

wherein R 1 , R 2 and R 3 have the meaning as given above
in the presence of a catalyst and in the presence of a liquid phase, wherein the liquid phase contains at least 25 weight-% water based on the total weight of the liquid phase, determined at a temperature of 20° C. and a pressure of 1 bar and wherein the oxidant is oxygen, and wherein the catalyst comprises platinum on a support and
the alpha, beta unsaturated aldehyde has a selectivity (based on the alcohol of general formula (II)) in the range of over 90%.

2. The process according to claim 1 , wherein an alcohol according to formula (II) is used, wherein R 3 is H and R 2 and R 1 are CH 3 .

3. The process according to claim 1 , wherein the liquid phase contains at least 50 weight-% water based on the total weight of the liquid phase.

4. The process according to claim 1 , wherein the oxidation is carried out at a temperature of 20° C. to 100° C.

5. The process according to claim 1 , wherein the oxidation is carried out under a partial pressure of oxygen between 0.2 and 8 bar.

6. The process according to claim 2 , wherein the liquid phase contains at least 50 weight % water based on the total weight of the liquid phase.

7. The process according to claim 1 , wherein the liquid phase contains at least 70 weight % water based on the total weight of the liquid phase.

8. The process according to claim 2 , wherein the liquid phase contains at least 70 weight % water based on the total weight of the liquid phase.

9. The process according to claim 2 , wherein the oxidation is carried out at a temperature of 20° C. to 100° C.

10. The process according to claim 3 , wherein the oxidation is carried out at a temperature of 20° C. to 100° C.

11. The process according to claim 1 , wherein the oxidation is carried out at a temperature of 20° C. to 70° C.

12. The process according to claim 2 , wherein the oxidation is carried out at a temperature of 20° C. to 70° C.

13. The process according to claim 3 , wherein the oxidation is carried out at a temperature of 20° C. to 70° C.

14. The process according to claim 8 , wherein the oxidation is carried out at a temperature of 20° C. to 70° C.

15. The process according to claim 2 , wherein the oxidation is carried out under a partial pressure of oxygen between 0.2 and 8 bar.

16. The process according to claim 14 , wherein the oxidation is carried out under a partial pressure of oxygen between 0.2 and 8 bar.

17. The process according to claim 1 , wherein said catalyst comprises a promotor, which enhance the activity of the catalytically active metal.

18. The process according to claim 1 , wherein said promotor is bismuth (Bi), antimony (Sb), lead (Pb), cadmium (Cd), tin (Sn) or tellurium (Te).

19. The process according to claim 1 , wherein the alpha, beta unsaturated aldehyde has a selectivity (based on the alcohol of general formula (II)) in the range of over 93%.

20. The process according to claim 1 , wherein the alpha, beta unsaturated aldehyde has a selectivity (based on the alcohol of general formula (II)) in the range of over 95%.

21. The process according to claim 1 , wherein the alpha, beta unsaturated aldehyde has a selectivity (based on the alcohol of general formula (II)) in the range of over 97%.

22. The process according to claim 1 , wherein the alpha, beta unsaturated aldehyde has a selectivity (based on the alcohol of general formula (II)) in the range of over 99%.

Assignees

• Basf Se

Inventors

• Vautravers Nicolas
• Teles Joaquim Henrique
• Keller Andreas
• Fenyn Michaela

Classifications

• C07C45/38 Primary

  being a primary hydroxyl group · CPC title

• B01J21/18

  Carbon · CPC title

• B01J23/42

  Platinum · CPC title