Process for beta-lactone production

Patent metadata

Field	Value
Publication number	US-9493391-B2
Application number	US-201514857313-A
Country	US
Kind code	B2
Filing date	Sep 17, 2015
Priority date	Apr 8, 2009
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.

First claim

We claim:

1. A continuous method of making poly(3-hydroxy propionic acid) from ethylene oxide, the method comprising steps of:
reacting the contents of a feed stream comprising ethylene oxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a liquid reaction product stream comprising beta-propiolactone and a carbonylation catalyst;
separating at least a portion of the beta-propiolactone in the reaction product stream from the carbonylation catalyst to produce a liquid catalyst recycling stream comprising carbonylation catalyst;
polymerizing at least a portion of the separated beta-propiolactone to produce poly(3-hydroxy propionic acid); and
adding the liquid catalyst recycling stream to the feed stream.

2. A continuous method of making poly(3-hydroxy propionic acid) from ethylene oxide, the method comprising steps of:
reacting the contents of a feed stream comprising ethylene oxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a liquid reaction product stream comprising beta-propiolactone and a carbonylation catalyst;
returning the liquid reaction product stream to the feed stream until the weight percent of beta-propiolactone in the liquid reaction product stream is in the range of about 10% to about 90%; and
then separating at least a portion of the beta-propiolactone in the reaction product stream from the carbonylation catalyst to produce a liquid catalyst recycling stream comprising carbonylation catalyst;
polymerizing at least a portion of the separated beta-propiolactone to produce poly(3-hydroxy propionic acid); and
adding the liquid catalyst recycling stream to the feed stream.

3. The method of claim 1 , further comprising treating the poly(3-hydroxy propionic acid) under conditions to convert the poly(3-hydroxy propionic acid) into a compound selected from the group consisting of acrylic acid, acrylates, acrylamide, and polyacrylates.

4. The method of claim 1 , further comprising treating the poly(3-hydroxy propionic acid) under conditions to convert the poly(3-hydroxy propionic acid) into a compound selected from the group consisting of acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, and 2-ethylhexyl acrylate.

5. The method of claim 1 , further comprising treating the poly(3-hydroxy propionic acid) under conditions to convert the poly(3-hydroxy propionic acid) into acrylic acid.

6. The method of claim 1 , wherein, upon reacting, the solvent has a boiling point that is higher than the boiling point of the beta-propiolactone when the solvent and beta-propiolactone are at the same pressure.

7. The method of claim 1 , wherein the liquid catalyst recycling stream comprises beta-propiolactone.

8. The method of claim 1 , wherein the liquid reaction product stream comprises ethylene oxide.

9. The method of claim 8 , wherein the liquid reaction product stream comprises an amount of ethylene oxide sufficient to prevent anhydride formation.

10. The method of claim 9 , wherein the liquid reaction product stream comprises at least about 0.1% ethylene oxide by weight.

11. The method of claim 1 , further comprising treating the liquid catalyst recycling stream, prior to the adding step, by adding fresh carbonylation catalyst, removing spent carbonylation catalyst, adding solvent, adding ethylene oxide, adding a portion of the separated beta-propiolactone, or a combination thereof.

12. The method of claim 1 , wherein the separating step comprises volatilizing at least a portion of the beta-propiolactone from the liquid reaction product stream to produce the separated beta-propiolactone.

13. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to reduced pressure.

14. The method of claim 13 , wherein the reduced pressure is between about 5Torr and about 500 Torr.

15. The method of claim 13 , wherein the reduced pressure is between about 10Torr and about 100 Torr.

16. The method of claim 13 , wherein the reduced pressure is sufficient to reduce the boiling point of the beta-propiolactone by about 20 to about 100 ° C. below its boiling point at atmospheric pressure.

17. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to elevated temperature.

18. The method of claim 17 , wherein the elevated temperature is greater than the boiling point of the beta-propiolactone but less than the boiling point of the solvent.

19. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to reduced pressure and elevated temperature.

20. The method of claim 12 , further comprising a step of condensing beta-propiolactone from the separated beta-propiolactone.

21. The method of claim 1 , further comprising adding beta-propiolactone to the feed stream.

22. The method of claim 21 , wherein the beta-propiolactone added to the feed stream is taken from the separated beta-propiolactone.

23. The method of claim 22 , wherein the beta-propiolactone is added to the feed stream until the weight percent of beta-propiolactone in the liquid reaction product stream is in the range of about 10% to about 90%, and the method then comprises withdrawing beta-propiolactone from the liquid reaction product stream while maintaining the weight percent of beta-propiolactone in the liquid reaction product stream in the range of about 10% to about 90%.

24. The method of claim 1 , wherein the boiling point of the solvent is at least 20° C. higher than the boiling point of the beta-propiolactone.

25. The method of claim 1 , wherein the solvent has a boiling point of at least 172° C. at atmospheric pressure.

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

27. The method of claim 26 , wherein the metal carbonyl compound has the general formula [QM y (CO) w ] x ,
where: Q is any ligand and need not be present;
M is a metal atom;
y is an integer from 1 to 6 inclusive;
w is a number that provides a metal carbonyl compound that is stable; and
x is an integer from −3 to +3 inclusive.

28. The method of claim 27 , wherein M is selected from the group consisting of Ti, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Cu, Zn, Al, Ga and In.

29. The method of claim 27 , wherein M is Co.

30. The method of claim 27 , wherein M is Co, y is 1, and w is 4.

31. The method of claim 27 , wherein the metal carbonyl compound comprises a carbonyl cobaltate and the carbonylation catalyst further comprises a Lewis acidic co-catalyst which comprises a metal-centered cationic Lewis acid.

32. The method of claim 31 , wherein the metal-centered cationic Lewis acid comprises an aluminum cation.

33. The method of claim 1 , wherein the liquid reaction product stream comprises carbon monoxide and ethylene oxide and the separating step comprises:
separating the liquid reaction product stream into i) a gaseous stream comprising carbon monoxide and ethylene oxide, and ii) a liquid stream comprising beta-propiolactone and carbonylation catalyst; and
separating the liquid stream comprising beta-propiolactone and carbonylation catalyst into i) the separated beta-propiolactone; and ii) the liquid catalyst recycling stream comprising carbonylation catalyst.

Assignees

• Novomer Inc

Inventors

• Allen Scott D
• Valente Ronald R
• Lee Han
• Cherian Anna E
• Bunning Donald L
• Clinton Nye A
• Fruchey Olan Stanley
• Dombek Bernard Duane

Classifications

• C08G63/08

  Lactones or lactides · CPC title

• C07D307/60 Primary

  Two oxygen atoms, e.g. succinic anhydride · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title

• C07C67/30

  by modifying the acid moiety of the ester, such modification not being an introduction of an ester group · CPC title

• C07C51/377 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · CPC title