IP Library Granted Patent US 11,827,590
Granted Patent B2
US 11,827,590 · App. 17/152,248 · Granted Nov 28, 2023

Acrylic acid, and methods of producing thereof

Inventors: Sadesh H. Sookraj (Rochester, NY); Alexander Tseitlin (Rochester, NY)
Assignee: Novomer, Inc.
C07C51/09B01J4/001B01J8/0278B01J20/267B01J20/3085B01J29/084B01J29/40C07C51/44C07C51/50C07D305/12C08F20/06C08F120/06B01J2208/00752
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Quick Facts
Patent No.
US 11,827,590
App. No.
17/152,248
Granted
Nov 28, 2023
Kind
B2
Abstract

Provided herein are methods of producing acrylic acid from beta-propiolactone. Such methods may involve the use of a heterogeneous catalyst, such as a zeolite.

Claims (24)

1. A method of producing acrylic acid from beta-propiolactone, comprising:

combining beta-propiolactone, a zeolite, and a polymerization inhibitor;

producing acrylic acid from at least a portion of the beta-propiolactone;

wherein the beta-propiolactone, the polymerization inhibitor, and the zeolite are combined neat or with a polar aprotic solvent; and wherein the produced acrylic acid has a purity of at least 95% and a yield of at least 90%.

2. The method of claim 1 , the zeolite is an acidic zeolite.

3. The method of claim 1 , wherein the zeolite is Zeolite Y or Zeolite ZSM-5, or a combination thereof.

4. The method of claim 1 , wherein the polymerization inhibitor is phenothiazine.

5. The method of claim 1 , wherein the acrylic acid produced is continuously isolated.

6. The method of claim 1 , wherein the acrylic acid is produced at a temperature of between 170° C. and 200° C.

7. The method of claim 1 , wherein the beta-propiolactone, the polymerization inhibitor, and the zeolite are further combined with the polar aprotic solvent.

8. The method of claim 7 , wherein the polar aprotic solvent comprises sulfolane.

9. The method of claim 1 , wherein the acrylic acid produced has a purity of greater than 95%.

10. The method of claim 1 , further comprising isolating acrylic acid.

11. The method of claim 10 , wherein the acrylic acid is isolated by distillation.

12. The method of claim 1 , further comprising contacting an epoxide compound with carbon monoxide to form beta-propiolactone.

13. A method of producing acrylic acid from beta-propiolactone, comprising:

contacting epoxide compound and carbon monoxide to form beta-propiolactone,

combining beta-propiolactone, a zeolite, a polymerization inhibitor, and a polar aprotic solvent;

producing acrylic acid from at least a portion of the beta-propiolactone;

wherein the epoxide compound comprises ethylene oxide; and wherein the produced acrylic acid has a purity of at least 95% and a yield of at least 90%.

14. The method of claim 13 , wherein the zeolite comprises Zeolite Y, and the solvent comprises sulfolane.

15. The method of claim 12 , wherein the epoxide compound comprises ethylene oxide.

16. The method of claim 1 , further comprises stripping off at least a portion of the acrylic acid produced.

17. The method of claim 1 , wherein the beta-propiolactone, the polymerization inhibitor, and the zeolite are combined neat.

Assignments (4)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2022
From: TRUIST BANK
To: NOVOMER, INC.
Reel/Frame 061088/0116 →
SECURITY INTEREST Recorded Feb 1, 2022
From: NOVOMER, INC.
To: TRUIST BANK
Reel/Frame 058922/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2021
From: SOOKRAJ, SADESH H.; TSEITLIN, ALEXANDER
To: NOVOMER, INC.
Reel/Frame 054955/0221 →
Continuity (3)
Continuation 16087051
Provisional Application 62311262 · Mar 21, 2016
Related Publication 20210139402A1 · May 13, 2021