IP Library Granted Patent US 11,155,511
Granted Patent B2
US 11,155,511 · App. 16/932,338 · Granted Oct 26, 2021

Distillation process for production of acrylic acid

Inventor: Sadesh H. Sookraj (Rochester, NY)
Assignee: Novomer, Inc.
C07C51/09B01J19/2435C07C51/44C07C57/04C08G63/08C08G63/823B01J2219/24Y02P20/10
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Quick Facts
Patent No.
US 11,155,511
App. No.
16/932,338
Granted
Oct 26, 2021
Kind
B2
Abstract

Provided are integrated processes for the conversion of beta propiolactone to acrylic acid. Systems for the production of acrylic acid are also provided.

Claims (41)

1. A method for producing acrylic acid, comprising:

(a) filtering a solvent stream and a beta propiolactone stream through a membrane;

(b) contacting the solvent stream and the beta propiolactone stream in a first reaction zone in a presence of a polymerization catalyst;

(c) polymerizing a poly(propiolactone) from the beta propiolactone stream, the solvent stream, and the polymerization catalyst in a second reaction zone;

(d) decomposing, by thermolysis, the poly(propiolactone) into acrylic acid in the reaction zone; and

(e) distilling a distillation stream, comprising the solvent steam, and a product stream, comprising the acrylic acid, from the reaction zone.

2. The method of claim 1 , wherein the polymerization catalyst is a homogeneous catalyst, and wherein the solvent stream comprises the polymerization catalyst.

3. The method of claim 2 , further comprising:

withdrawing a recycle stream comprising the polymerization catalyst so that the polymerization catalyst can be reused in the reaction zone.

4. The method of claim 1 , wherein the beta propiolactone stream further comprises another solvent, and wherein the method further comprises:

distilling a recycle stream comprising the solvent of the beta propiolactone stream; and

directing the recycle stream to a carbonylation reactor that is configured to produce the beta propiolactone stream.

5. The method of claim 4 , wherein the solvent of the beta propiolactone stream is a non-protic solvent, a hydrocarbon, or an ether, and wherein the solvent of the beta propiolactone stream is usable in carbonylation of beta propiolactone.

6. The method of claim 1 , further comprising:

directing the distillation stream to a recycling tank so that the solvent of the solvent stream is reusable in the reaction zone.

7. The method of claim 1 , wherein the solvent of the solvent stream is a non-protic polar solvent, and wherein the poly(propiolactone) is soluble in the solvent of the solvent stream.

8. The method of claim 1 , wherein the polymerization catalyst is a carboxylate salt of a cation, wherein the cation includes a positive charge that is on a metal, metal oxide, salts of alkali and alkaline earth metals, borates, silicates, or salts of other metals.

9. The method of claim 1 , wherein the polymerization catalyst is a heterogeneous catalyst and the polymerization catalyst has a form of a fixed or packed bed.

10. The method of claim 1 , wherein the product stream has an acrylic acid content of at least about 99.5%.

11. A system, comprising:

(a) a membrane that is configured to filter a beta propiolactone stream and a solvent stream; and

(b) a reaction zone downstream of the membrane, the reaction zone is a single distillation column and is configured to:

(i) receive the beta propiolactone stream and the solvent stream;

(ii) concurrently polymerize beta propiolactone of the beta propiolactone stream to poly(propiolactone) in a presence of a polymerization catalyst and thermally decompose the poly(propiolactone) to acrylic acid; and

(iii) output a distillation stream, comprising a solvent of the solvent stream, and a product stream, comprising the acrylic acid; and

wherein the polymerization catalyst is a homogeneous catalyst, and wherein the solvent stream comprises the polymerization catalyst.

12. The system of claim 11 , wherein the reaction zone is configured to output a recycle stream, and wherein the recycle stream comprises the polymerization catalyst.

13. The system of claim 11 , wherein the beta propiolactone stream further comprises another solvent, and wherein the reaction zone is configured to output a recycle stream comprising the solvent of the beta propiolactone stream.

14. The system of claim 13 , wherein the solvent of the beta propiolactone stream is a non-protic polar solvent, and wherein the solvent of the beta propiolactone is recyclable in a carbonylation reactor that is upstream of a reactor zone.

15. A system, comprising:

(a) a membrane that is configured to filter a beta propiolactone stream and a solvent stream; and

(b) a reaction zone downstream of the membrane, the reaction zone is a single distillation column and is configured to:

(i) receive the beta propiolactone stream and the solvent stream;

(ii) concurrently polymerize beta propiolactone of the beta propiolactone stream to poly(propiolactone) in a presence of a polymerization catalyst and thermally decompose the poly(propiolactone) to acrylic acid; and

(iii) output a distillation stream, comprising a solvent of the solvent stream, and a product stream, comprising the acrylic acid;

wherein the polymerization catalyst is a heterogeneous catalyst, and wherein the polymerization catalyst has a form of a fixed or packed bed.

16. The system of claim 11 , wherein the solvent of the solvent stream is a non-protic polar solvent, and wherein the poly(propiolactone) is soluble in the solvent of the solvent stream.

17. The system of claim 11 , wherein the product stream has an acrylic acid content of at least about 99.5%.

18. The system of claim 11 , wherein the polymerization catalyst is a carboxylate salt of a cation, wherein the cation includes a positive charge that is on a nitrogen atom, a sulfur atom, a phosphorus atom, or any combination thereof.

19. The system of claim 18 , wherein the polymerization catalyst is a carboxylate salt of a protonated amine, a quaternary ammonium, guanidinium, sulfonium, arsonium, a substituted nitrogen-containing heterocycle cation, a phosphorus cation, or any combination thereof.

20. The system of claim 15 , wherein the polymerization catalyst is a carboxylate salt of a cation, wherein the cation includes a positive charge that is on a nitrogen atom, a sulfur atom, a phosphorus atom, or any combination thereof, and the polymerization catalyst is a carboxylate salt of a protonated amine, a quaternary ammonium, guanidinium, sulfonium, arsonium, a substituted nitrogen-containing heterocycle cation, a phosphorus cation, or any combination thereof.

Assignments (3)
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 Oct 8, 2020
From: SOOKRAJ, SADESH H.
To: NOVOMER, INC.
Reel/Frame 054008/0842 →
Continuity (4)
Continuation 16107881 · Aug 21, 2018
Continuation 15550243
Provisional Application 62116328 · Feb 13, 2015
Related Publication 20200347004A1 · Nov 5, 2020