IP Library Granted Patent US 11,807,613
Granted Patent B2
US 11,807,613 · App. 17/386,627 · Granted Nov 7, 2023

Integrated methods for chemical synthesis

Inventors: Sadesh H. Sookraj (Rochester, NY); Michael A. Slowik (Waltham, MA)
Assignee: Novomer, Inc.
C07D305/12C01B3/50C07D307/60C10G2/30C01B2203/062C01B2203/066Y02E50/30Y02P20/10
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Quick Facts
Patent No.
US 11,807,613
App. No.
17/386,627
Granted
Nov 7, 2023
Kind
B2
Abstract

The integrated processes herein provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming. Provided are also ethylene oxide carbonylation products such as beta-propiolactone and succinic anhydride having a bio-based content between 0% and 100%, and methods for producing and analyzing the same.

Claims (41)

1. A method for creating a composition of beta-propiolactone or succinic anhydride comprising:

carbonylating ethylene oxide using carbon monoxide;

wherein at least one of the ethylene oxide or the carbon monoxide has a bio-based carbon content greater than zero percent and a pMC greater than zero, and optionally at least one of the ethylene oxide or the carbon monoxide has a fossil-based carbon content; to produce beta-propiolactone with a pMC of about 35.8 to about 107.5, or succinic anhydride with a pMC of about 27 to about 107.5.

2. The method of claim 1 , wherein the carbon monoxide has a pMC of 107.5 or the ethylene oxide has a pMC of 107.5.

3. The method of claim 1 , wherein one of the ethylene oxide and carbon monoxide has a bio-based carbon content greater than zero percent, and the other has a bio-based carbon content of less than 100 percent.

4. The method of claim 3 , wherein the ethylene oxide has a bio-based carbon content of 100 percent or the carbon monoxide has a bio-based carbon content of 100 percent.

5. The method of claim 1 , wherein the beta-propiolactone has three carbon atoms;

wherein two of the three carbon atoms in the beta-propiolactone are bio-based carbon and the third carbon atom is fossil-based carbon; and

wherein the beta-propiolactone has a pMC of about 71.7.

6. The method of claim 5 , wherein the carbonyl carbon of the beta-propiolactone is fossil-based carbon.

7. The method of claim 1 , wherein the beta-propiolactone has three carbon atoms;

wherein one of the three carbon atoms in the beta-propiolactone is bio-based carbon and the other two carbons atom are fossil-based carbon; and

wherein the beta-propiolactone has a pMC of about 35.8.

8. The method of claim 7 , wherein the carbonyl carbon of the beta-propiolactone is bio-based carbon.

9. The method of claim 1 , wherein the succinic anhydride has four carbon atoms;

wherein two of the four carbon atoms of the succinic anhydride are bio-based carbon and two of the carbon atoms are fossil-based carbon; and

wherein the succinic anhydride has a pMC of about 54.

10. The method of claim 9 , wherein the two carbonyl carbon atoms of the succinic anhydride are bio-based carbon.

11. The method of claim 9 , wherein the two carbonyl carbon atoms of the succinic anhydride are fossil-based carbon.

12. A composition comprising:

beta-propiolactone having bio-based carbon, and optionally fossil-based carbon;

wherein the beta-propiolactone has a pMC of about 35.8 to about 107.5.

13. The composition of claim 12 , wherein the beta-propiolactone has three carbon atoms;

wherein the carbon atoms are bio-based carbon and fossil-based carbon; and

wherein the beta-propiolactone has a pMC of about 35.8 to about 71.7.

14. The composition of claim 13 , wherein two of the three carbon atoms are bio-based carbon and the third carbon atom is fossil-based carbon; and

wherein the beta-propiolactone has a pMC of about 71.7.

15. The composition of claim 13 , wherein two of the three carbon atoms are fossil-based carbon and the third carbon atom is bio-based carbon; and

wherein the beta-propiolactone has a pMC of about 35.8.

16. A composition comprising:

succinic anhydride having bio-based carbon, and optionally fossil-based carbon;

wherein the succinic anhydride has a pMC of about 27 to about 107.5.

17. The composition of claim 16 , wherein the succinic anhydride has four carbon atoms:

wherein the carbon atoms are bio-based carbon and fossil-based carbon; and

wherein the succinic anhydride has a pMC of about 27 to about 80.

18. The composition of claim 17 , wherein two of the four carbon atoms of the succinic anhydride are bio-based carbon and two of the carbon atoms are fossil-based carbon; and

wherein the succinic anhydride has a pMC of about 54.

19. The composition of claim 17 , wherein three of the four carbon atoms of the succinic anhydride are bio-based carbon and one of the carbon atoms is fossil-based carbon; and

wherein the succinic anhydride has a pMC of about 80.

20. The composition of claim 17 , wherein three of the four carbon atoms of the succinic anhydride are fossil-based carbon and one of the carbon atoms is bio-based carbon; and

wherein the succinic anhydride has a pMC of about 27.

Assignments (2)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2021
From: SOOKRAJ, SADESH H.; SLOWIK, MICHAEL A.
To: NOVOMER, INC.
Reel/Frame 057860/0364 →
Continuity (4)
Continuation 16453775 · Jun 26, 2019
Continuation 15550300
Provisional Application 62116109 · Feb 13, 2015
Related Publication 20210403446A1 · Dec 30, 2021