IP Library Granted Patent US 10,577,297
Granted Patent B2
US 10,577,297 · App. 16/204,572 · Granted Mar 3, 2020

Method for obtaining alcohols from aldehydes

Inventors: Dirk Fridag (Haltern am See, DE); Robert Franke (Marl, DE); Michael Grass (Haltern am See, DE); Florian Boeck (Düsseldorf, DE); Corinna Hecht (Haltern am See, DE); Benedikt Dercks (Bochum, DE); Udo Lenz (Recklinghausen, DE); Christoph Hiller (Dülmen, DE); Christoph Ehlers (Münster, DE); Stefan Münzner (Dorsten, DE)
Assignee: Evonik Operations GmbH
C07C29/175C07C29/141C07C29/80C07C29/82C07C45/50C07C45/74B01J31/185B01J2531/822
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Quick Facts
Patent No.
US 10,577,297
App. No.
16/204,572
Granted
Mar 3, 2020
Kind
B2
Abstract

The present invention relates to a method for preparing saturated C n - and C 2n -alcohols, wherein the separation of the C n -alcohols and the C 2n -alcohols is effected by means of at least one two-column system or by means of at least one dividing wall column.

Claims (24)

1. A method for preparing saturated and C 2n -alcohols where n=4, 5 and 6 comprising the method steps of

a) aldol condensation of isomeric C n -aldehydes where n=4, 5 and 6 to obtain a mixture of C n - and α,β-unsaturated C 2n -aldehydes, wherein the proportion of unbranched aldehydes is at least 20% by weight, based on the C n -aldehydes used where n=4, 5 and 6

b) hydrogenating the mixture of C n - and α,β-unsaturated C 2n -aldehydes obtained in a) with hydrogen to obtain a mixture of saturated C n and C 2n -alcohols and

c) phase separating the mixture of C n and C 2n -alcohols,

wherein the separation of the C n -alcohols and the C 2n -alcohols is effected by means of at least one two-column system or by means of at least one dividing wall column, wherein the isomer ratio of the C n -alcohol obtained is adjusted by the aldol condensation carried out in step a), wherein the proportion of linear C n -alcohols is at least 2 mol % and less than 60 mol %, based on the mixture of isomeric C n -alcohols, and wherein during phase separating, bottoms including the C n -alcohols having a water content of less than 1000 ppm.

2. The method according to claim 1 , wherein the C n -aldehydes where n=4, 5 and 6 used in step a) were prepared by hydroformylation of isomeric olefins having 3 to 5 carbon atoms with synthesis gas in the presence of a hydroformylation catalyst to form the aldehydes specified.

3. The method according to claim 2 , wherein in the hydroformylation a catalyst system is used which comprises rhodium as central atom and is complexed with the ligand (1):

4. The method according to claim 1 , wherein the aldol condensation in step a) is carried out in the presence of aqueous sodium hydroxide solution.

5. The method according to claim 1 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a tubular reactor which comprises at least one mixing module which disperses the reactant aldehyde into droplets having an average diameter (Sauter diameter) of 0.2 mm to 2 mm in the continuous catalyst phase (process liquor), which consists of aqueous sodium hydroxide solution and sodium salts of carboxylic acids and has a sodium content of 0.6 to 1.75% by mass and a pH in the range from 12.5 to 13.5.

6. The method according to claim 1 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a temperature range of from 100 to 150° C.

7. The method according to claim 1 , wherein a reaction pressure in a reactor during the aldol condensation of the C n -aldehydes according to step a) is in a range from 0.2 to 1.0 MPa.

8. The method according to claim 1 , wherein the hydrogenation according to step b) is carried out in a temperature range from 170° C. to 200° C. at a pressure of 15*10 5 Pa to 30*10 5 Pa over a supported catalyst which contains at least nickel and copper as active components.

9. The method according to claim 1 , wherein a hydrogenation according to step b) is carried out with hydrogen in a pressure range from 5 to 100 bar and the hydrogenation temperatures are between 120 and 220° C.

10. The method according to claim 1 , wherein n=5.

11. The method according to claim 2 , wherein the aldol condensation in step a) is carried out in the presence of aqueous sodium hydroxide solution.

12. The method according to claim 3 , wherein the aldol condensation in step a) is carried out in the presence of aqueous sodium hydroxide solution.

13. The method according to claim 2 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a tubular reactor which comprises at least one mixing module which disperses the reactant aldehyde into droplets having an average diameter (Sauter diameter) of 0.2 mm to 2 mm in the continuous catalyst phase (process liquor), which consists of aqueous sodium hydroxide solution and sodium salts of carboxylic acids and has a sodium content of 0.6 to 1.75% by mass and a pH in the range from 12.5 to 13.5.

14. The method according to claim 3 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a tubular reactor which comprises at least one mixing module which disperses the reactant aldehyde into droplets having an average diameter (Sauter diameter) of 0.2 mm to 2 mm in the continuous catalyst phase (process liquor), which consists of aqueous sodium hydroxide solution and sodium salts of carboxylic acids and has a sodium content of 0.6 to 1.75% by mass and a pH in the range from 12.5 to 13.5.

15. The method according to claim 2 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a temperature range from 100 to 150° C.

16. The method according to claim 3 , wherein the aldol condensation of the C n -aldehydes according to step a) is carried out in a temperature range from 100 to 150° C.

17. The method according to claim 2 , wherein a reaction pressure in a reactor during the aldol condensation of the C n -aldehydes according to step a) is in a range from 0.2 to 1.0 MPa.

18. The method according to claim 2 , wherein the hydrogenation according to step b) is carried out in a temperature range from 170° C. to 200° C. at a pressure of 15*10 5 Pa to 30*10 5 Pa over a supported catalyst which contains at least nickel and copper as active components.

19. The method according to claim 1 , wherein a hydrogenation according to step b) is carried out with hydrogen in a pressure range from 5 to 100 bar and the hydrogenation temperatures are between 120 and 220° C.

20. The method according to claim 2 , wherein n=5.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065692/0785 →
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2019
From: FRIDAG, DIRK; FRANKE, ROBERT; GRASS, MICHAEL; BOECK, FLORIAN; HECHT, CORINNA; DERCKS, BENEDIKT; LENZ, UDO; HILLER, CHRISTOPH; EHLERS, CHRISTOPH; MÜNZNER, STEFAN
To: EVONIK DEGUSSA GMBH
Reel/Frame 048743/0684 →
Priority Claims (1)
EP 17204995 · Dec 1, 2017 · regional
Continuity (1)
Related Publication 20190169106A1 · Jun 6, 2019
Cited By (2)
US 12,221,404 US 12,521,644