PROCESS FOR BETA-LACTONE PRODUCTION

• US 20140275575A1
• Filed: 05/12/2014
• Published: 09/18/2014
• Est. Priority Date: 04/08/2009
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Lee, Han, Cherian, Anna E., Bunning, Donald L., Clinton, Nye A., Fruchey, Olan Stanley, Dombek, Bernard Duane, Allen, Scott D., Valente, Ronald R.
• Granted Patent: US 9,206,144 B2
• Time in Patent Office: Days
• US Class Current: 549/328
• CPC Class Codes: C07C 231/14 by formation of carboxamide groups together with reactions not involving the carboxamide groups
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 51/377 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups C07C51/36 - C07C51/373 take precedence
• CPC Class Codes: C07C 67/30 by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
• CPC Class Codes: C07C 67/317 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: Y02P 20/584 Recycling of catalysts

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.

Claims

1. A method comprising steps of:

reacting the contents of a feed stream comprising an epoxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a reaction product stream comprising a beta-lactone;

separating at least a portion of the beta-lactone in the reaction product stream from the solvent and carbonylation catalyst to produce;

i) a beta-lactone stream comprising beta-lactone, and

ii) a catalyst recycling stream comprising carbonylation catalyst and solvent; and

adding the catalyst recycling stream to the feed stream.

2. The method of claim 1, further comprising treating the beta-lactone stream under conditions to convert the beta lactone into a compound selected from the group consisting of:

acrylic acid;

acrylates;

acrylamide; and

polyacrylates.

15. The method of claim 1, wherein the reaction product stream comprises a portion of the epoxide.

16. The method of claim 15, wherein the reaction product stream comprises sufficient epoxide to prevent anhydride formation.

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

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

39. 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 lactone.

42. The method of claim 1, wherein the epoxide has the formula

43. The method of claim 1, wherein the epoxide is chosen from the group consisting of:

ethylene oxide;

propylene oxide;

1,2-butylene oxide;

2,3-butylene oxide;

epichlorohydrin;

cyclohexene oxide;

cyclopentene oxide;

3,3,3-Trifluoro-1,2-epoxypropane, styrene oxide;

a glycidyl ether; and

a glycidyl ester.

44. The method of claim 1, wherein the epoxide comprises ethylene oxide.

45. The method of claim 1, wherein the epoxide comprises propylene oxide.

46. The method of claim 2, wherein the treating step is performed in the presence of a compound selected from the group consisting of:

an alcohol, an amine and a thiol, under conditions that produce the corresponding acrylic ester, acrylamide, or a thioacrylate respectively.

47. The method of claim 2, wherein the treating step is performed in the presence of a compound of formula H—

Y to afford an acrylate having the formula

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

63. The method of claim 62, 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 such as to provide the stable metal carbonyl; and

x is an integer from −

3 to +3 inclusive.

78. The method of claim 2, wherein the treating step is mediated by a catalyst.

79. The method of claim 78, wherein the catalyst in the treating step is an acid catalyst.

80. The method of claim 78, wherein the catalyst in the treating step is a basic catalyst.

91. The method of claim 1, wherein the carbon monoxide in the reacting step is supplied as an industrial gas stream comprising carbon monoxide and one or more additional gases.

3-14. -14. (canceled)

17-23. -23. (canceled)

25-27. -27. (canceled)

29-38. -38. (canceled)

40. (canceled)

41. (canceled)

48-61. -61. (canceled)

64-77. -77. (canceled)

81-90. -90. (canceled)

92-110. -110. (canceled)

111. A method comprising steps of:

reacting the contents of a feed stream comprising an epoxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a reaction product stream comprising a beta-lactone;

returning the entirety of the reaction product stream to the feed stream until the weight percent of beta-lactone in the reaction product stream is in a predetermined range;

then separating at least a portion of the beta-lactone in the reaction product stream from the solvent and carbonylation catalyst to produce;

i) a beta-lactone stream comprising beta-lactone, and

ii) a catalyst recycling stream comprising the carbonylation catalyst and the solvent; and

adding the catalyst recycling stream to the feed stream.

112-114. -114. (canceled)