CATALYST RECYCLE METHODS

• US 20170096407A1
• Filed: 04/29/2015
• Published: 04/06/2017
• Est. Priority Date: 05/05/2014
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: SOOKRAJ, Sadesh H.
• Granted Patent: US 10,858,329 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 31/20 Carbonyls
• CPC Class Codes: B01J 31/2217 At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
• CPC Class Codes: B01J 31/403 containing iron group metals or copper
• CPC Class Codes: B01J 38/74 utilising ion-exchange
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: Y02P 20/584 Recycling of catalysts

Abstract

The present invention provides novel solutions to the problem of recycling carbonylation catalysts in epoxide carbonylation processes. The inventive methods are characterized in that the catalyst is recovered in a form other than as active catalyst. In some embodiments, catalyst components are removed selectively from the carbonylation product stream in two or more processing steps. One or more of these separated catalyst components are then utilized to regenerate active catalyst which is utilized during another time interval to feed a continuous carbonylation reactor.

Claims

1. A method for the continuous reaction of an epoxide and carbon monoxide comprising:

a) feeding a continuous carbonylation reactor during a first interval of time with a catalyst feed stream comprising a carbonylation catalyst, where within the reactor, ethylene oxide and carbon monoxide react in the presence of the carbonylation catalyst to provide a reaction product stream comprising an epoxide carbonylation product and carbonylation catalyst,

b) treating the reaction product stream to separate at least a portion of the carbonylation catalyst from the reaction product stream,

c) accumulating carbonylation catalyst collected in step (b) throughout the first interval of time to obtain a spent carbonylation catalyst batch, and

d) feeding a continuous carbonylation reactor during a second interval of time with a catalyst feed stream wherein at least a portion of the catalyst in the catalyst feed stream is derived from spent carbonylation catalyst batch accumulated in step (c).

2. The method of claim 1, wherein the epoxide is ethylene oxide.

3. The method of claim 2, wherein the epoxide carbonylation product is selected from the group consisting of:

beta propiolactone, succinic anhydride, polypropiolactone, 3-hydroxypropionic acid, and a 3-hydroxypropionate ester.

5. The method of claim 1, wherein the carbonylation catalyst comprises a metal carbonyl compound.

6. The method of claim 5, wherein step (b) comprises removing metal carbonyl from the reaction product stream.

7. The method of claim 1, wherein the carbonylation catalyst comprises a metal carbonyl compound in combination with one or more other catalyst components.

8. The method of claim 7, wherein step (b) comprises selectively removing metal carbonyl compound to the at least partial exclusion of other catalyst components.

9. The method of claim 1, wherein the metal carbonyl compound comprises an anionic metal carbonyl in combination with a cationic Lewis acid.

10. The method of claim 9, wherein step (b) comprises selectively removing at least a portion of the anionic metal carbonyl compound from the reaction product stream using an anion exchanging material.

11. The method of claim 9, wherein step (b) comprises selectively removing at least a portion of the cationic Lewis acid from the reaction product stream using a cation exchanging material.

12. The method of claim 9, wherein step (b) comprises treating the reaction product stream using an anion exchanging material to remove metal carbonyl and separately treating the reaction product stream using a cation exchanging material to remove Lewis acid.

4.