IP Library Granted Patent US 10,870,631
Granted Patent B2
US 10,870,631 · App. 16/615,720 · Granted Dec 22, 2020

Process for the epoxidation of propene

Inventors: Willi Hofen (Rodenbach, DE); Thomas Haas (Münster, DE); Wolfgang Wöll (Maintal, DE); Jürgen Schemel (Bad Soden, DE); Hans-Christian Dietz (Hattersheim, DE); Marc Brendel (Bruchköbel, DE)
Assignees: EVONIK OPERATIONS GMBH; THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
C07D301/12
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Quick Facts
Patent No.
US 10,870,631
App. No.
16/615,720
Granted
Dec 22, 2020
Kind
B2
Abstract

In a process for the epoxidation of propene, comprising continuously reacting a propene feed with hydrogen peroxide in the presence of an epoxidation catalyst in a reaction step, using propene in excess to hydrogen peroxide, to provide a liquid reaction mixture comprising non-reacted propene, extra safety measures caused by the presence of oxygen during work-up of the liquid reaction mixture of the epoxidation reaction can be avoided by stripping liquid reaction mixture from step a) with an inert gas to provide an oxygen depleted stripped liquid reaction mixture and a strip gas stream, selecting the amount of inert gas to provide an oxygen concentration in the strip gas stream in the range of from 0.1 to 10% by weight, separating non-reacted propene from the strip gas stream and recycling it to the reaction step, and separating propene oxide from the stripped liquid reaction mixture.

Claims (24)

1. A process for the epoxidation of propene, comprising:

a) continuously reacting a propene feed with hydrogen peroxide in the presence of an epoxidation catalyst in a reaction step, using propene in excess to hydrogen peroxide, to provide a liquid reaction mixture comprising non-reacted propene;

b) stripping the liquid reaction mixture from step a) with an inert gas in a counter-current stripping column to provide an oxygen depleted stripped liquid reaction mixture and a strip gas stream, wherein the amount of inert gas used is selected so as to provide an oxygen concentration in the strip gas stream in the range of from 0.1 to 10% by weight;

c) separating non-reacted propene from the strip gas stream obtained in step b) and recycling it to step a); and

d) separating propene oxide from the stripped liquid reaction mixture obtained in step b).

2. The process of claim 1 , wherein the amount of inert gas is selected to provide an oxygen concentration in the strip gas stream in the range of from 0.5 to 8% by weight.

3. The process of claim 1 , wherein step a) is carried out at a reaction pressure of at least 1.9 MPa and step b) is carried out at a pressure in the range of from 80% to 110% of the reaction pressure.

4. The process of claim 1 , wherein non-reacted propene is separated from the stripped liquid reaction mixture obtained in step b) and recycled to step a).

5. The process of claim 1 , wherein the liquid reaction mixture is heated to a constant temperature in the range of from 35 to 70° C. before or during stripping it in step b).

6. The process of claim 1 , wherein step a) is carried out under reaction conditions providing a two phase liquid reaction mixture comprising a propene rich liquid phase and a liquid reaction mixture rich in water, said propene rich liquid phase and said liquid reaction mixture rich in water are separated and the separated liquid reaction mixture rich in water is stripped in step b).

7. The process of claim 1 , wherein in step c) the strip gas stream is contacted with a liquid solvent to absorb propene into said solvent, providing a propene depleted gas stream and a propene loaded solvent, and said propene loaded solvent is passed to step a).

8. The process of claim 7 , wherein in step c) propene oxide is separated from the strip gas stream by partial condensation before said stream is contacted with said liquid solvent.

9. The process of claim 7 , wherein in step c) part of the propene contained in the strip gas stream is separated by condensation before said stream is contacted with said liquid solvent.

10. The process of claim 7 , wherein no component is separated from the strip gas stream before contacting it with said liquid solvent.

11. The process of claim 1 , wherein step a) is carried out with a heterogeneous epoxidation catalyst in a trickle bed reactor, inert gas is fed to said trickle bed reactor, a purge gas stream comprising inert gas and oxygen is withdrawn from said trickle bed reactor and said purge gas stream is combined with the strip gas stream between steps b) and c).

12. The process of claim 1 , wherein the inert gas is selected from nitrogen, argon, oxygen depleted air, methane and mixtures thereof.

13. The process of claim 1 , wherein step a) is carried out with a titanium zeolite catalyst in the presence of a solvent selected from the group consisting of: methanol, ethanol, tert-butanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, tetrahydrofuran, dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ethers, acetone, 2-butanone, acetonitrile and propionitrile.

14. The process of claim 13 , wherein step a) is carried out with a titanium silicalite catalyst in the presence of a methanol solvent.

15. The process of claim 10 , wherein step a) is carried out at a reaction pressure of at least 1.9 MPa and step b) is carried out at a pressure in the range of from 80% to 110% of the reaction pressure.

16. The process of claim 10 , wherein the amount of inert gas is selected to provide an oxygen concentration in the strip gas stream in the range of from 0.5 to 8% by weight.

17. The process of claim 10 , wherein step a) is carried out with a heterogeneous epoxidation catalyst in a trickle bed reactor, inert gas is fed to said trickle bed reactor, a purge gas stream comprising inert gas and oxygen is withdrawn from said trickle bed reactor and said purge gas stream is combined with the strip gas stream between steps b) and c).

18. The process of claim 11 , wherein step a) is carried out with a titanium zeolite catalyst in the presence of a solvent selected from the group consisting of methanol, ethanol, tert-butanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, tetrahydrofuran, dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ethers, acetone, 2-butanone, acetonitrile and propionitrile.

19. The process of claim 17 , wherein step a) in the process is carried out with a titanium silicalite catalyst in the presence of a methanol solvent.

20. The process of claim 19 , wherein the amount of inert gas is selected to provide an oxygen concentration in the strip gas stream in the range of from 0.5 to 8% by weight.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2024
From: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
To: THYSSENKRUPP UHDE GMBH
Reel/Frame 068439/0716 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 1, 2020
From: HOFEN, WILLI; HAAS, THOMAS; WÖLL, WOLFGANG; BRENDEL, MARC
To: EVONIK OPERATIONS GMBH
Reel/Frame 051396/0167 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 1, 2020
From: SCHEMEL, JÜRGEN; DIETZ, HANS-CHRISTIAN
To: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
Reel/Frame 051396/0181 →
Priority Claims (1)
EP 17172167 · May 22, 2017 · regional
Continuity (1)
Related Publication 20200109125A1 · Apr 9, 2020
Cited By (1)
US 12,459,881