Method for the epoxidation of an olefin with hydrogen peroxide

Patent metadata

Field	Value
Publication number	US-10196370-B2
Application number	US-201615550872-A
Country	US
Kind code	B2
Filing date	Feb 3, 2016
Priority date	Feb 17, 2015
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

In the method for the epoxidation of an olefin, the olefin is continuously reacted with hydrogen peroxide in a mixed reactor in the presence of a water soluble epoxidation catalyst, comprising a manganese complex, the reaction is carried out in a reaction mixture comprising an aqueous liquid phase and an organic liquid phase with mixing of the liquid phases, reaction mixture is continuously withdrawn from the mixed reactor and separated into a separated aqueous phase and a separated organic phase, and part of the separated aqueous phase is continuously recycled into the mixed reactor, with the combined hold-up time of aqueous phase in withdrawing, separating phases and recycling aqueous phase being kept at less than 15 minutes.

First claim

The invention claimed is:

1. A method for the epoxidation of an olefin, comprising:
a) continuously reacting the olefin with hydrogen peroxide in a mixed reactor in the presence of a water soluble epoxidation catalyst comprising a manganese complex, wherein the reaction is carried out in a reaction mixture comprising an aqueous liquid phase and an organic liquid phase with mixing of the liquid phases;
b) continuously withdrawing reaction mixture from the mixed reactor and separating the withdrawn reaction mixture into a separated aqueous phase and a separated organic phase; and
c) continuously recycling part of the separated aqueous phase into the mixed reactor by nanofiltration of the separated aqueous phase with a nanofiltration membrane providing a retentate enriched in manganese complex and recycling all or a part of said retentate into the mixed reactor;
wherein the combined hold-up time of aqueous phase in steps b) and c), defined as the ratio of the total volume occupied by aqueous phase in steps b) and c) to the volumetric flow rate of recycled separated aqueous phase, is less than 15 minutes.

2. The method of claim 1 , wherein in step b) the withdrawn reaction mixture is separated with a centrifuge.

3. The method of claim 2 , wherein the centrifuge provides an acceleration of at least 50 000 ms −2 .

4. The method of claim 2 , wherein the centrifuge is a conical plate centrifuge.

5. The method of claim 1 , wherein the nanofiltration is carried out with cross flow over the nanofiltration membrane.

6. The method of claim 1 , wherein the nanofiltration membrane comprises a separation layer made from a polyamide.

7. The method of claim 1 , wherein the mixed reactor is a loop reactor.

8. The method of claim 1 , wherein no acid is added except in step a).

9. The method of claim 1 , wherein the olefin is propene or allyl chloride.

10. The method of claim 1 , wherein the manganese complex comprises a 1,4,7-trimethyl-1,4,7-triazacyclonane ligand.

11. The method of claim 1 , wherein the reaction is carried out in the presence of an oxalate buffer.

12. The method of claim 1 , wherein in step a), the pH of the aqueous liquid phase is maintained in the range from 2.5 to 5.

13. The method of claim 9 , wherein the manganese complex comprises a 1,4,7-trimethyl-1,4,7-triazacyclonane ligand.

14. The method of claim 13 , wherein the reaction is carried out in the presence of an oxalate buffer.

15. The method of claim 14 , wherein in step a) the pH of the aqueous liquid phase is maintained in the range from 2.5 to 5.

16. The method of claim 15 , wherein the nanofiltration is carried out with cross flow over the nanofiltration membrane.

Assignees

• Evonik Degussa Gmbh

Inventors

• Stock Jürgen
• André Joao
• Imm Sebastian
• Pascaly Matthias

Classifications

• C07C11/04

  Ethene · CPC title

• C07C21/067

  Allyl chloride; Methallyl chloride · CPC title

• C07D301/12 Primary

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title

• C07C11/06

  Propene · CPC title

• C07D303/02

  Compounds containing oxirane rings · CPC title