Process for preparing aldehydes and cooling a stream of matter

Patent metadata

Field	Value
Publication number	US-11820739-B2
Application number	US-202218055442-A
Country	US
Kind code	B2
Filing date	Nov 15, 2022
Priority date	Nov 19, 2021
Publication date	Nov 21, 2023
Grant date	Nov 21, 2023

Abstract

A process for preparing aldehydes by a homogeneously catalysed hydroformylation of C4 to C20 olefins involves withdrawing a biphasic stream (liquid/gaseous) and expanding in two stages. Before, between, or after the two stages, the liquid phase is cooled. Only after expansion and cooling is the homogeneously dissolved rhodium catalyst system separated from the residual stream.

First claim

The invention claimed is:

1. A process for preparing aldehydes by hydroformylation of olefins, the process comprising:
a) reacting C 4 to C 20 olefins in a hydroformylation in at least one reaction zone in the presence of a synthesis gas and a homogeneous rhodium catalyst system, at a pressure of 100 to 350 bar and a temperature of 90° C. to 250° C., to obtain a biphasic hydroformylation mixture comprising a gas phase and a liquid phase, wherein the biphasic hydroformylation mixture contains at least unconverted olefins, the synthesis gas, the homogeneous rhodium catalyst system and aldehydes formed, and which is withdrawn from the at least one reaction zone;
b) expanding the biphasic hydroformylation mixture in a first expansion, to a pressure between 11 bar and 50 bar, and separating the biphasic hydroformylation mixture into a first gaseous phase comprising the synthesis gas, and a first liquid phase comprising the unconverted olefins, the homogeneous rhodium catalyst system, the aldehydes formed, and optionally, remaining synthesis gas;
c) expanding the first liquid phase obtained from b) in a second expansion, to a pressure between 10 mbar and 10 bar, and separating the first liquid phase into a second gaseous phase comprising the remaining synthesis gas, and a second liquid phase comprising the unconverted olefins, the homogeneous rhodium catalyst system, and the aldehydes formed; and
d) feeding the second liquid phase to a removal, comprising a thermal separation to remove the aldehydes formed and a membrane separation to remove the homogeneous rhodium catalyst system,
wherein the biphasic hydroformylation mixture prior to the first expansion in b), the first liquid phase prior to the second expansion in c), or the second liquid phase prior to the feeding to a removal in d) is cooled to a temperature between 40 and 100° C.

2. The process according to claim 1 , wherein the biphasic hydroformylation mixture prior to the first expansion in b) is cooled.

3. The process according to claim 1 , wherein the hydroformylation in a) is effected at a pressure between 175 and 300 bar.

4. The process according to claim 1 , wherein the hydroformylation in a) is effected at a temperature in a range from 120 to 200° C.

5. The process according to claim 1 , wherein the C 4 to C 20 olefins used in the hydroformylation function as solvent.

6. The process according to claim 1 , wherein the homogeneous rhodium catalyst system used in the hydroformylation comprises rhodium and a phosphorus-containing ligand.

7. The process according to claim 1 , wherein the first expansion in b) and/or the second expansion in c) is into a vessel in which gas phase and liquid phase can be separated.

8. The process according to claim 1 , wherein the cooling is effected by a discharge cooler.

9. The process according to claim 1 , wherein the membrane separation in d) is effected at a temperature between 20 and 80° C.

10. The process according to claim 1 , wherein a transmembrane pressure in the membrane separation in d) is between 15 and 50 bar.

11. The process according to claim 1 , wherein the homogeneous rhodium catalyst system is obtained in a retentate in the membrane separation in d), and the retentate is returned to the at least one reaction zone in a).

12. The process according to claim 1 , wherein the thermal separation is a distillation, a thin-film evaporation, a falling-film evaporation, or a combination of two or more thereof.

13. The process according to claim 12 , wherein the thermal separation is the thin-film evaporation, the falling-film evaporation, or a combination of thin-film evaporation and falling-film evaporation.

14. The process according to claim 13 , wherein the second expansion in c) is into a vacuum.

15. The process according to claim 1 , wherein the aldehydes obtained from the process are sent to a downstream process.

16. The process according to claim 1 , wherein the C 4 to C 20 olefins are C 8 to C 12 olefins.

17. The process according to claim 1 , wherein the membrane separation is a multistage membrane separation.

18. The process according to claim 1 , wherein the biphasic hydroformylation mixture prior to the first expansion in b), the first liquid phase prior to the second expansion in c), or the second liquid phase prior to the feeding to a removal in d) is cooled to a temperature between 50 and 95° C.

19. The process according to claim 1 , wherein the biphasic hydroformylation mixture prior to the first expansion in b), the first liquid phase prior to the second expansion in c), or the second liquid phase prior to the feeding to a removal in d) is cooled to a temperature between 60 and 90° C.

20. The process according to claim 15 , wherein the downstream process is a hydrogenation or an oxidation.

Assignees

• Evonik Operations Gmbh

Inventors

• Markovic Ana
• Geilen Frank
• Brächer Alexander
• Dercks Benedikt
• Drees Stefan
• Weber Tonia
• Franke Robert
• Fridag Dirk

Classifications

• C07C45/50 Primary

  by oxo-reactions · CPC title

• B01J23/464

  Rhodium · CPC title

• B01J27/14

  Phosphorus; Compounds thereof · CPC title

• C07C45/62

  by hydrogenation of carbon-to-carbon double or triple bonds · CPC title

• C07C45/505 Primary

  Asymmetric hydroformylation · CPC title