Continuous carbonylation processes

• US 10,221,150 B2
• Filed: 02/12/2016
• Issued: 03/05/2019
• Est. Priority Date: 02/13/2015
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Farmer, Jay J., Galebach, Peter, Sherry, Kyle, Sookraj, Sadesh H.
• Primary Examiner(s): Oh, Taylor V
• Application Number:
  US15/550,217
• Publication Number:
  US 20180030015A1
• Time in Patent Office: 1,117 Days
• Field of Search: 549233
• CPC Class Codes: B01J 31/00 Catalysts comprising hydrides, coordination complexes or organic compounds catalyst compositions used only in polymerisation reactions C08 ; catalytic antibodies C12N9/0002
• CPC Class Codes: C07C 67/37 by reaction of ethers with carbon monoxide
• CPC Class Codes: C07C 69/67 of saturated acids
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride

Abstract

Provided are processes for monitoring and maintaining continuous carbonylation of epoxides or lactones. Processes include measuring parameters affecting the rate of the carbonylation reaction and adding supplemental replacement catalyst replacement components to maintain a constant rate of carbonylation.

Claims

1. A process for continuous carbonylation of an epoxide or lactone feedstock, comprising:

continuously reacting an epoxide or lactone feedstock with carbon monoxide in the presence of a carbonylation catalyst in a carbonylation reaction vessel,

wherein the carbonylation catalyst comprises a Lewis acid and a metal carbonyl, and

wherein at a start time of the process, the carbonylation reaction vessel contains an initial concentration of the Lewis acid and an initial concentration of the metal carbonyl; and

adding to the carbonylation reaction vessel, at a time after the start time of the process, a catalyst replacement component which is different from the carbonylation catalyst,

wherein the catalyst replacement component comprises the Lewis acid, a precursor to the Lewis acid, the metal carbonyl, and a precursor to the metal carbonyl,

wherein the precursor to the metal carbonyl is a neutral metal carbonyl complex, and

wherein the precursor to the Lewis acid is;

2. The process of claim 1, wherein a rate or time of addition of the catalyst replacement component is based on a rate of depletion of one or both of the Lewis acid and the metal carbonyl in the carbonylation reaction vessel.

3. The process of claim 2, wherein one or both of the Lewis acid and the metal carbonyl of the carbonylation catalyst depletes over time in the carbonylation reaction vessel, and the method further comprises determining the depletion,

wherein the depletion of one or both of the Lewis acid and the metal carbonyl in the carbonylation reaction vessel is determined by:

measuring one or more parameters selected from the group consisting of;

i-a) a concentration of the Lewis acid in the carbonylation reaction vessel;

i-b) a concentration of a decomposition product of the Lewis acid in the carbonylation reaction vessel;

ii-a) a concentration of the Lewis acid in a process stream downstream from the carbonylation reaction vessel;

ii-b) a concentration of a decomposition product of the Lewis acid in a process stream downstream from the carbonylation reaction vessel;

iii-a) a concentration of the metal carbonyl in the carbonylation reaction vessel;

iii-b) a concentration of a decomposition product of the metal carbonyl in the carbonylation reaction vessel;

iv-a) a concentration of the metal carbonyl in a process stream downstream from the carbonylation reaction vessel;

iv-b) a concentration of a decomposition product of the metal carbonyl in a process stream downstream from the carbonylation reaction vessel; and

v) a rate of the carbonylation reaction; and

obtaining a measured value of the one or more parameters.

4. The process of claim 3, further comprising:

comparing the measured value of the one or more parameters to a predetermined reference value for each parameter; and

determining a rate of addition or a time of addition of the catalyst replacement component based on the comparison.

5. The process of claim 4, wherein:

the rate of addition of the metal carbonyl or a precursor to the metal carbonyl is increased when the value of a measurement in parameter iii-b, iv-a, or iv-b, or any combination thereof, is greater than the predetermined value for each parameter;

the rate of addition of the metal carbonyl or a precursor to the metal carbonyl is increased when the value of a measurement in parameter iii-a is less than the predetermined value for the parameter;

the rate of addition of the Lewis acid or a precursor to the Lewis Acid is increased when the value of a measurement in parameter i-b, ii-a, or ii-b, or any combination thereof, is greater than the predetermined value for each parameter; and

the rate of addition of the Lewis acid or a precursor to the Lewis acid is increased when the value of a measurement in parameter i-a is less than the predetermined value for the parameter.

6. The process of claim 1, wherein the reacting of the epoxide or lactone feedstock with the carbon monoxide in the presence of the carbonylation catalyst in the carbonylation reaction vessel produces carbonylation products in a carbonylation product stream, and

the process further comprises separating the carbonylation product stream from the carbonylation reaction vessel.

7. The process of claim 6, wherein the carbonylation product stream is separated from the carbonylation reaction vessel by a nanofiltration membrane, and wherein the nanofiltration membrane retains at least a portion of the Lewis acid and the metal carbonyl, and permeates the carbonylation products.

8. The process of claim 1, wherein the precursor to the metal carbonyl is Co₂(CO)₈ or Co₄(CO)₁₂.

9. The process of claim 1, wherein the catalyst replacement component is added directly to the carbonylation reaction vessel.

10. The process of claim 1, wherein the catalyst replacement component is recycled from a carbonylation product stream, an intermediate carbonylation process stream, or a process stream downstream of the carbonylation reaction vessel.

11. The process of claim 3, wherein the one or more parameters are measured continuously.

12. The process of claim 1, wherein the catalyst replacement component is added continuously.

13. The process of claim 1, wherein the catalyst replacement component is added intermittently.

16. The process of claim 1, wherein the epoxide feedstock is continuously reacted with the carbon monoxide in the presence of the carbonylation catalyst in the carbonylation reaction vessel.

17. The process of claim 1, wherein the epoxide feedstock comprises ethylene oxide.

18. The process of claim 1, wherein the precursor to the Lewis acid is

19. The process of claim 1, wherein the precursor to the Lewis acid is

20. The process of claim 1, wherein the precursor to the Lewis acid is

21. The process of claim 1, wherein the precursor to the Lewis acid is

22. The process of claim 1, wherein the precursor to the Lewis acid is

23. The process of claim 1, wherein the precursor to the Lewis acid is

24. The process of claim 1, wherein the precursor to the Lewis acid is

25. The process of claim 1, wherein M is aluminum, chromium, titanium, indium, gallium, zinc, cobalt, or copper.

26. The process of claim 1, wherein M is aluminum or chromium.

27. The process of claim 1, wherein the catalyst replacement components have a halide content less than about 200 ppm.

29. The process of claim 1, wherein each R^q is independently C_1-12 aliphatic.

14. A process for continuous carbonylation of an epoxide or lactone feedstock, comprising:

continuously reacting an epoxide or lactone feedstock with carbon monoxide in the presence of a catalyst in a carbonylation reaction vessel, wherein the catalyst comprises a Lewis acid and a metal carbonyl; and

continuously or intermittently introducing to the carbonylation reaction vessel a catalyst replacement component which is different from the carbonylation catalyst, wherein the catalyst replacement component comprises a species selected from the group consisting of the Lewis acid, a precursor to the Lewis acid, the metal carbonyl, and a precursor to the metal carbonyl,

wherein the precursor to the metal carbonyl is a neutral metal carbonyl complex, and

wherein the precursor to the Lewis acid is;

15. The process of claim 14, wherein the catalyst replacement component is introduced at a rate that results in less than 10% variation in the rate of the carbonylation reaction over a period of one hour.

30. The process of claim 14, wherein each R^q is independently C_1-12 aliphatic.

28. A process for continuous carbonylation of an epoxide or lactone feedstock, comprising:

continuously reacting an epoxide or lactone feedstock with carbon monoxide in the presence of a carbonylation catalyst in a carbonylation reaction vessel to produce a carbonylation product stream,

wherein the carbonylation catalyst comprises a Lewis acid and a metal carbonyl,

wherein the carbonylation product stream comprises at least one carbonylation product, at least some of the Lewis acid and at least some of the metal carbonyl, and

wherein at a start time of the process, the carbonylation reaction vessel contains an initial concentration of the Lewis acid and an initial concentration of the metal carbonyl;

separating the carbonylation product stream from the carbonylation reaction vessel by a nanofiltration membrane,

wherein the nanofiltration membrane retains at least a portion of the Lewis acid and at least a portion of the metal carbonyl, and permeates at least one carbonylation product; and

adding to the carbonylation reaction vessel, at a time after the start time of the process, a catalyst replacement component which is different from the carbonylation catalyst,

wherein the catalyst replacement component is added at a rate or time of addition based on a rate of depletion of one or both of the Lewis acid and the metal carbonyl in the carbonylation reaction vessel,

wherein the catalyst replacement component comprises the Lewis acid, a precursor to the Lewis acid, the metal carbonyl, and a precursor to the metal carbonyl,

wherein the precursor to the metal carbonyl is a neutral metal carbonyl complex, and

wherein the precursor to the Lewis acid is;

31. The process of claim 28, wherein each R^q is independently C_1-12 aliphatic.