Process and system for production of polypropiolactone

• US 10,662,283 B2
• Filed: 02/12/2016
• Issued: 05/26/2020
• 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): Truong, Duc
• Application Number:
  US15/550,234
• Publication Number:
  US 20180030201A1
• Time in Patent Office: 1,565 Days
• Field of Search: 528354
• CPC Class Codes: B01D 3/14 Fractional distillation or use of a fractionation or rectification column
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/823 for the preparation of polylactones or polylactides
• CPC Class Codes: Y02P 20/10 Process efficiency

Abstract

Provided are integrated processes for the conversion of ethylene oxide to polypropiolactone. Systems for the production of polypropiolactone are also provided.

Claims

1. A continuous method for producing polypropiolactone (PPL), comprising:

providing feedstock streams of ethylene oxide (EO) and carbon monoxide, wherein the feedstock streams are optionally combined;

directing the feedstock streams to a first reaction zone;

contacting the feedstock streams with a carbonylation catalyst in the presence of a carbonylation solvent in the first reaction zone to convert at least a portion of the EO to a beta propiolactone (BPL) product stream, wherein the BPL product stream comprises BPL, carbonylation catalyst, and carbonylation solvent;

separating at least a portion of carbonylation catalyst from the BPL product stream to produce a carbonylation catalyst recycling stream and a processed BPL product stream, wherein the processed BPL product stream comprises BPL and carbonylation solvent;

directing the processed BPL product stream to a carbonylation solvent removal zone;

removing at least a portion of the carbonylation solvent from the processed BPL product stream to produce a polymerization feed stream, wherein the polymerization feed stream comprises BPL;

directing the polymerization feed stream to a second reaction zone;

introducing a polymerization solvent into the polymerization feed stream, prior to contacting the polymerization feed stream with a polymerization catalyst in the second reaction zone, wherein the polymerization solvent is different from the carbonylation solvent; and

contacting BPL in the polymerization feed stream with the polymerization catalyst in the second reaction zone to produce PPL.

2. The method of claim 1, wherein the removing of at least a portion of the carbonylation solvent from the processed BPL product stream comprises distilling at least a portion of the carbonylation solvent and withdrawing a distillation stream of the carbonylation solvent.

3. The method of claim 1, wherein the carbonylation solvent has a boiling point below 160°

C. at 1 atm.

4. The method of claim 1, wherein the second reaction zone is a reactive extruder.

5. The method of claim 1, wherein the separating of at least a portion of carbonylation catalyst from the BPL product stream comprises nanofiltration on a nanofiltration membrane.

6. The method of claim 1, further comprising returning the carbonylation catalyst recycling stream returned to the first reaction zone.

7. The method of claim 1, wherein heat is generated from contacting of the BPL in the polymerization feed stream with the polymerization catalyst, wherein at least a portion of the heat is used to maintain a temperature of the second reaction zone.

8. The method of claim 1, wherein heat is generated from contacting of the BPL in the polymerization feed stream with the polymerization catalyst, and the method further comprises capturing at least a portion of the heat, and directing the captured heat to other processes.

9. The method of claim 8, wherein the heat is directed to the distillation of the carbonylation solvent.

10. The method of claim 1, wherein the polymerization feed stream is neat when introduced into the second reaction zone.

11. The method of claim 1, wherein the polymerization catalyst is a salt of a compound of formula:

12. The method of claim 1, wherein the polymerization catalyst is a salt of a compound of formula:

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

14. The method of claim 1, wherein the carbonylation solvent comprises a polar donating solvent.

15. The method of claim 1, wherein the polymerization solvent is less polar than the carbonylation solvent as measured by dielectric constant.

16. The method of claim 1, wherein the polymerization solvent has a dielectric constant at 20°

C. of less than about 13.6.

17. The method of claim 1, wherein the polymerization solvent comprises a Lewis base and is less polar than 1,3-dioxane, ortho-difluorobenzene, or metadifluorobenzene.

18. The method of claim 1, wherein the polymerization solvent comprises a Lewis base with substantially a same polarity as 1,4-dioxane.