Process for beta-lactone production
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.
1. A continuous method of making a beta-propiolactone from ethylene oxide, the method comprising steps of:
reacting, in a reactor, 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 carbonylation catalyst;
separating, outside the reactor, at least a portion of the beta-propiolactone in the reaction product stream from the carbonylation catalyst to produce:
i) a beta-propiolactone stream comprising beta-propiolactone, and
ii) a liquid catalyst recycling stream comprising carbonylation catalyst; and
adding the liquid catalyst recycling stream to the feed stream;
the method further comprising: treating the beta-propiolactone stream under conditions to convert the beta-propiolactone into a compound selected from the group consisting of acrylic acid, acrylates, acrylamide, and polyacrylates.
2. A continuous method of making a beta-propiolactone from ethylene oxide, the method comprising steps of:
reacting, in a reactor, 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 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, outside the reactor, at least a portion of the beta-propiolactone in the liquid reaction product stream from the carbonylation catalyst to produce:
i) a beta-propiolactone stream comprising beta-propiolactone, and
ii) a liquid catalyst recycling stream comprising carbonylation catalyst; and
adding the liquid catalyst recycling stream to the feed stream.
3. The method of claim 1 , further comprising treating the beta-propiolactone stream under conditions to convert the beta-propiolactone into a compound selected from the group consisting of acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, and 2-ethylhexyl acrylate.
4. The method of claim 1 , further comprising treating the beta-propiolactone stream under conditions to convert the beta-propiolactone into acrylic acid.
5. The method of claim 1 , wherein at the same pressure the solvent has a boiling point that is higher than the boiling point of the beta-propiolactone.
6. The method of claim 1 wherein the liquid catalyst recycling stream comprises beta-propiolactone.
7. The method of claim 1 , wherein the liquid reaction product stream comprises ethylene oxide.
8. The method of claim 7 , wherein the liquid reaction product stream comprises an amount of ethylene oxide sufficient to prevent anhydride formation.
9. The method of claim 8 , wherein the liquid reaction product stream comprises at least about 0.1% ethylene oxide by weight.
10. 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 beta-propiolactone taken from the beta-propiolactone stream, or a combination thereof.
11. 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 beta-propiolactone stream.
12. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to reduced pressure.
13. The method of claim 12 , wherein the reduced pressure is between about 5 Torr and about 500 Torr.
14. The method of claim 12 , wherein the reduced pressure is between about 10 Torr and about 100 Torr.
15. The method of claim 12 , 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.
16. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to elevated temperature.
17. The method of claim 16 , wherein the elevated temperature is greater than the boiling point of the beta-propiolactone but less than the boiling point of the solvent.
18. The method of claim 1 , wherein the separating step comprises exposing the liquid reaction product stream to reduced pressure and elevated temperature.
19. The method of claim 11 , further comprising a step of condensing beta-propiolactone from the beta-propiolactone stream.
20. The method of claim 1 , further comprising adding beta-propiolactone to the feed stream.
21. The method of claim 20 , wherein the beta-propiolactone added to the feed stream is taken from the beta-propiolactone stream.
22. The method of claim 21 , 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%.
23. 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.
24. The method of claim 23 , wherein the solvent has a boiling point of at least 172° C. at atmospheric pressure and the beta-propiolactone is beta-propiolactone.
25. The method of claim 1 , wherein the carbonylation catalyst comprises a metal carbonyl compound.
26. The method of claim 25 , 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.
27. The method of claim 26 , wherein M is selected from the group consisting of Ti, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Cu, Zn, Al, Ga and In.
28. The method of claim 26 , wherein M is Co.
29. The method of claim 26 , wherein M is Co, y is 1, and w is 4.
30. The method of claim 26 , 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.
31. The method of claim 30 , wherein the metal-centered cationic Lewis acid comprises an aluminum cation.
32. 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 into i) the beta-propiolactone stream comprising beta-propiolactone; and ii) the liquid catalyst recycling stream comprising carbonylation catalyst.
33. The method of claim 32 , wherein the solvent has a boiling point higher than the boiling point of the beta-propiolactone and the catalyst recycling stream further comprises solvent.
34. The method of claim 32 , further comprising the step of returning the gaseous stream comprising carbon monoxide and ethylene oxide to the feed stream.
35. The method of claim 32 , wherein the solvent has a boiling point lower than the boiling point of the beta-propiolactone and the gaseous stream comprising carbon monoxide and ethylene oxide further comprises solvent.
36. The method of claim 1 , wherein the liquid reaction product stream is returned to the feed stream until the weight percent of beta-propiolactone in the liquid reaction product stream is in the range of about 43% to about 53%, 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 43% to about 53%.
37. The method of claim 1 , wherein the beta-propiolactone stream is gaseous.
38. The method of claim 2 , wherein the beta-propiolactone stream is gaseous.
39. The method of claim 1 , wherein the carbonylation catalyst is [(ClTPP)Al] + [Co(CO)4] − .
40. The method of claim 2 , wherein the carbonylation catalyst is [(ClTPP)Al] + [Co(CO)4] − .