Process for the production of acid anhydrides from epoxides

• US 9,403,788 B2
• Filed: 02/12/2013
• Issued: 08/02/2016
• Est. Priority Date: 02/13/2012
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Lee, Han, Slowik, Michael A.
• Primary Examiner(s): SHAMEEM, GOLAM M
• Application Number:
  US14/378,290
• Publication Number:
  US 20150005513A1
• Time in Patent Office: 1,267 Days
• Field of Search: 549/231, 549/233
• US Class Current: 1/1
• CPC Class Codes: B01J 2231/48 Ring-opening reactions
• CPC Class Codes: B01J 2531/31 Aluminium
• CPC Class Codes: B01J 2531/845 Cobalt
• CPC Class Codes: B01J 31/2295 Cyclic compounds, e.g. cyclopentadienyls
• CPC Class Codes: C07D 303/12 with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride

Abstract

A method of making acid anhydrides from epoxide and carbon monoxide feedstocks is presented. In various aspects, the method includes steps of reacting the contents of a feed stream comprising an epoxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a first carbonylation product stream comprising a beta-lactone, then reacting the contents of the first carbonylation product stream with additional carbon monoxide to produce a second carbonylation product stream comprising an acid anhydride, and separating at least a portion of the acid anhydride from the second carbonylation product stream to produce: i) an acid anhydride product stream comprising the separated portion of acid anhydride; and ii) a recycling stream comprising the carbonylation catalyst, and finally adding the recycling stream to the feed stream.

Claims

1. A method for the continuous production of an acid anhydride, the method comprising the steps of:

a) contacting an epoxide with carbon monoxide, optionally in the presence of a carbonylation catalyst in a first reaction zone to provide a first product stream comprising a beta-lactone, residual epoxide, and, if present, the carbonylation catalyst;

b) feeding the first product stream to a second reaction zone, where the stream is contacted with additional carbon monoxide under conditions sufficient to convert substantially all of the residual epoxide to the beta-lactone and to convert a portion of the beta-lactone to an acid anhydride, to provide a second product stream comprising dissolved acid anhydride and, if present, carbonylation catalyst;

c) treating the second product stream such that the concentration of the acid anhydride in the stream exceeds the solubility of the acid anhydride;

d) separating solid acid anhydride from the second product stream to produce an acid anhydride product stream comprising solid acid anhydride and a liquid catalyst recycling stream comprising the dissolved catalyst, if present, and dissolved acid anhydride; and

e) returning the liquid catalyst recycling stream to an inlet of the first reaction zone, wherein the acid anhydride is a succinic anhydride.

2. The method according to claim 1 for the continuous production of succinic anhydride, the method comprising the steps of:

a) contacting ethylene oxide with carbon monoxide in the presence of a carbonylation catalyst in a first reaction zone to provide a first product stream comprising beta propiolactone, residual ethylene oxide, and the carbonylation catalyst;

b) feeding the first product stream to a second reaction zone, where the stream is contacted with additional carbon monoxide under conditions sufficient to convert substantially all of the residual ethylene oxide to beta propiolactone and to convert at least a portion of the beta propiolactone to succinic anhydride, to provide a second product stream comprising dissolved succinic anhydride and carbonylation catalyst;

c) treating the second product stream such that the concentration of succinic anhydride in the stream exceeds the solubility of succinic anhydride;

d) separating solid succinic anhydride from the second product stream to produce a succinic anhydride product stream comprising solid succinic anhydride and a liquid catalyst recycling stream comprising the dissolved catalyst and dissolved succinic anhydride; and

e) returning the liquid catalyst recycling stream to an inlet of the first reaction zone.

3. The method of claim 1, wherein the first reaction zone comprises at least one continuous stirred tank reactor.

4. The method of claim 3, wherein at least one continuous stirred tank reactor in the first reaction zone is operated at steady state conditions.

5. The method of claim 3, wherein the first reaction zone comprises a series of two or more continuous stirred tank reactors where each reactor is characterized in that it has a lower steady state epoxide concentration than the reactor preceding it in the series.

6. The method of claim 1, wherein the second reaction zone comprises one or more plug flow reactors.

7. The method of claim 6, wherein the at least one plug flow reactor in the second reaction zone is operated under conditions to convert essentially all of the beta-lactone in the reaction zone to acid anhydride.

8. The method of claim 1, wherein the first reaction zone comprises at least one continuous stirred tank reactor and the second reaction zone comprises at least one plug flow reactor.

9. The method of claim 1, wherein the first reaction zone comprises a plurality of continuous stirred tank reactors and the second reaction zone comprises at least one plug flow reactor.

10. The method of claim 1, wherein the second reaction zone is operated at higher CO pressure and/or higher temperature than the first reaction zone.

11. The method of claim 1, wherein the second reaction zone is operated at an elevated temperature.

12. The method of claim 11, wherein the step of treating the second product stream comprises cooling the stream.

13. The method of claim 12, wherein the second product stream is cooled by between about 10°

C. and about 120°

C.

14. The method of claim 13, wherein the second product stream is cooled by between about 20°

C. and about 100°

C., between about 20°

C. and about 80°

C., between about 10°

C. and about 60°

C., or between about 20°

C. and about 40°

C.

15. The method of claim 12, wherein the second product stream is cooled by about 10°

C., about 20°

C., about 30°

C., about 40°

C., about 60°

C., about 80°

C., or about 100°

C.

16. The method of claim 1, wherein the step of treating the second product stream comprises contacting the stream with seed crystals of the acid anhydride.

17. The method of claim 1, wherein the step of separating solid acid anhydride from the second product stream comprises filtering the stream to remove solid acid anhydride.

18. The method of claim 17, wherein the filtration is performed under a CO atmosphere.

19. The method of claim 18, wherein the filtration is performed under a CO pressure in the range from about 15 psi to about 5000 psi.

20. The method of claim 19, wherein the filtration is performed under a CO pressure in the range from about 15 psi to about 1200 psi, from about 60 psi to about 800 psi, from about 100 psi to about 600 psi, from about 200 psi to about 600 psi, or from about 50 psi to about 500 psi.

21. The method of claim 17, wherein the filtering step provides a filtrate comprising the liquid catalyst recycling stream characterized in that it is saturated in the acid anhydride.

22. The method of claim 21, wherein the filtrate is heated before the step of returning it to an inlet of the first reaction zone.

23. The method of claim 1, characterized in that steps a) and b) are performed in the presence of a solvent.

24. The method of claim 23, wherein the solvent comprises 1,4 dioxane.

25. The method of claim 1, wherein the carbonylation catalyst comprises metal carbonyl compound and a Lewis acid.

26. The method of claim 1, wherein the carbonylation catalyst comprises an anionic metal carbonyl compound and a cationic Lewis acid.

27. The method of claim 26, wherein the anionic metal carbonyl compound comprises Co(CO)₄⁻

.

28. The method of claim 26, wherein the cationic Lewis acid comprises the combination of a metal atom and a multidentate ligand.

29. The method of claim 28, wherein the cationic Lewis acid comprises the combination of a metal atom in the 3+ oxidation state and a dianionic tetradentate ligand.

30. The method of claim 26, wherein the cationic Lewis acid comprises aluminum.

31. The method of claim 26, wherein the cationic Lewis acid comprises chromium.

32. The method of claim 26, wherein the cationic Lewis acid comprises an optionally substituted porphyrin ligand.

33. The method of claim 26, wherein the cationic Lewis acid comprises an optionally substituted salen ligand.

34. The method of claim 26, wherein the cationic Lewis acid comprises an optionally substituted salph ligand.

35. The method of claim 2, wherein the first reaction zone contains a liquid reaction mixture at steady state, the liquid reaction mixture comprising a mixture of 1,4 dioxane, ethylene oxide, beta propiolactone, succinic anhydride and a metal carbonyl catalyst.

36. The method of claim 35, wherein the 1,4 dioxane comprises from about 10 weight percent to about 95 weight percent of the reaction mixture, the beta propiolactone comprises from about 1 to about 90 weight percent of the mixture, the ethylene oxide comprises from about 0.01 to about 10 weight percent of the mixture, and the succinic anhydride comprises from about 4 to about 50 weight percent of the mixture.

37. The method of claim 1, further comprising the step of removing a fraction of the catalyst recycling stream from the system.

38. The method of claim 37, wherein the quantity of catalyst removed is replaced by a feed of fresh catalyst.

39. The method of claim 1, wherein the succinic anhydride is selected from the group consisting of succinic anhydride, methylsuccinic anhydride, chloromethylsuccinic anhydride, and ethylsuccinic anhydride.