IP Library Granted Patent US 10,125,108
Granted Patent B2
US 10,125,108 · App. 15/570,167 · Granted Nov 13, 2018

Process for the epoxidation of propene

Inventors: Robert Jahn (Rodenbach, DE); Wolfgang Wöll (Maintal, DE); Bernd Jaeger (Bickenbach, DE); Matthias Pascaly (Frankfurt, DE)
Assignees: EVONIK DEGUSSA GMBH; THYSSENKRUPP INDUSTRIAL SOLUTIONS
C07D301/12B01D3/34B01D3/4294B01D19/0409B01J29/89C07D301/36C07D303/04
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Quick Facts
Patent No.
US 10,125,108
App. No.
15/570,167
Granted
Nov 13, 2018
Kind
B2
Abstract

In a process for the epoxidation of propene, comprising the steps: reacting propene with hydrogen peroxide in the presence of a titanium silicalite catalyst and a methanol solvent; separating non-reacted propene and propene oxide from the resulting reaction mixture to provide a solvent mixture comprising methanol and water in a combined amount of at least 90% by weight; and feeding this solvent mixture as a feed stream to a continuously operated methanol distillation column at a feed point in the middle section of said column to provide an overhead product comprising at least 90% by weight methanol and a bottoms product comprising at least 90% by weight water; the addition of a liquid defoamer, having a solubility in the feed stream of less than 10 mg/kg at 25° C. and a surface tension at the liquid air interface of less than 22 mN/m at 20° C., at or above the feed point in an amount exceeding the solubility of the liquid defoamer in the feed stream suppresses foam formation in the methanol distillation column.

Claims (24)

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

a) reacting propene with hydrogen peroxide in the presence of a titanium silicalite catalyst and a methanol solvent;

b) separating non-reacted propene and propene oxide from the reaction mixture obtained in step a) to provide a solvent mixture comprising methanol and water with a combined amount of methanol and water of at least 90% by weight; and

c) feeding the solvent mixture obtained in step b) as a feed stream to a continuously operated methanol distillation column at a feed point in the middle section of said column providing an overhead product comprising at least 90% by weight methanol and a bottoms product comprising at least 90% by weight water;

wherein a liquid defoamer having a solubility in the feed stream of less than 10 mg/kg at 25° C. and a surface tension at the liquid air interface of less than 22 mN/m at 20° C. is added to the distillation column at or above the feed point in an amount exceeding the solubility of the liquid defoamer in the feed stream.

2. The process of claim 1 , wherein the liquid defoamer comprises a polydimethylsiloxane.

3. The process of claim 2 , wherein the liquid defoamer comprises more than 5% by weight polydimethylsiloxane.

4. The process of claim 1 , wherein the liquid defoamer comprises hydrophobized silica particles.

5. The process of claim 1 , wherein the liquid defoamer is added in an amount of from 2 to 50 wppm calculated on the feed stream.

6. The process of claim 1 , wherein the overhead product obtained in step c) is recycled to step a).

7. The process of claim 1 , wherein the liquid defoamer is added to the feed stream before feeding said feed stream to the methanol distillation column.

8. The process of claim 1 , wherein ammonia is added in step a).

9. The process of claim 1 , wherein an acid is added in step c) at or above the feed point in an amount sufficient to protonate all ammonia and amines contained in the feed stream.

10. The process of claim 9 , wherein the acid is added admixed with the liquid defoamer.

11. The process of claim 3 , wherein the liquid defoamer comprises hydrophobized silica particles.

12. The process of claim 3 , wherein the liquid defoamer is added in an amount of from 2 to 50 wppm calculated on the feed stream.

13. The process of claim 3 , wherein the overhead product obtained in step c) is recycled to step a).

14. The process of claim 3 , wherein the liquid defoamer is added to the feed stream before feeding said feed stream to the methanol distillation column.

15. The process of claim 3 , wherein ammonia is added in step a).

16. The process of claim 3 , wherein an acid is added in step c) at or above the feed point in an amount sufficient to protonate all ammonia and amines contained in the feed stream.

17. The process of claim 13 , wherein the liquid defoamer is added to the feed stream before feeding said feed stream to the methanol distillation column.

18. The process of claim 13 , wherein the liquid defoamer is added to the feed stream before feeding said feed stream to the methanol distillation column.

19. The process of claim 13 , wherein ammonia is added in step a).

20. The process of claim 13 , wherein an acid is added in step c) at or above the feed point in an amount sufficient to protonate all ammonia and amines contained in the feed stream.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2024
From: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
To: THYSSENKRUPP UHDE GMBH
Reel/Frame 068465/0992 →
CHANGE OF NAME Recorded Jan 10, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051621/0777 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2018
From: EVONIK DEGUSSA GMBH
To: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
Reel/Frame 046557/0386 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2017
From: JAHN, ROBERT; WÖLL, WOLFGANG; JAEGER, BERND; PASCALY, MATTHIAS
To: EVONIK DEGUSSA GMBH
Reel/Frame 044219/0913 →
Priority Claims (1)
EP 15165410 · Apr 28, 2015 · regional
Continuity (1)
Related Publication 20180134676A1 · May 17, 2018