Thermolysis of polypropiolactone to produce acrylic acid

• US 10,065,914 B1
• Filed: 04/24/2017
• Issued: 09/04/2018
• Est. Priority Date: 04/24/2017
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Ruhl, John, Sherry, Kyle Evan
• Primary Examiner(s): Zucker, Paul A
• Application Number:
  US15/494,805
• Time in Patent Office: 498 Days
• CPC Class Codes: B01J 19/0066 Stirrers mixing per se B01F
• CPC Class Codes: B01J 19/18 Stationary reactors having moving elements inside B01J19/08, B01J19/26 take precedence
• CPC Class Codes: B01J 19/2405 provoking a turbulent flow of the reactants, such as in cyclones, or having a high Reynolds-number
• CPC Class Codes: B01J 2219/00051 Controlling the temperature
• CPC Class Codes: B01J 2219/24 Stationary reactors without moving elements inside
• 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 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 305/14 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C08G 63/78 Preparation processes

Abstract

The present invention is directed to reactor apparatus and processes for thermolysis of polypropiolactone to produce highly pure acrylic acid. In preferred embodiments of the present invention, the processes comprise introducing a feed stream comprising polypropiolactone to a thermolysis process vessel through an inlet; maintaining a concentration of active salt by adding and removing portions of active salt by at least one inlet and at least one outlet; heating the thermolysis process vessel; and recovering a product including acrylic acid from an outlet. In certain preferred embodiments, the active salt may be present as a catalyst used for polymerization of the polypropiolactone in the feed stream. In some embodiments, one or more active salts may be added to the feed stream and/or the thermolysis process vessel.

Claims

1. A process for producing acrylic acid from a feed stream containing polypropiolactone, the process comprising:

a. passing the feed stream to a decomposition chamber of a thermolysis process vessel;

b. maintaining an active salt comprising sodium acrylate in the decomposition chamber of the thermolysis vessel at a predetermined concentration range wherein a portion of the active salt is removed from the decomposition chamber;

c. contacting the feed stream with the active salt in the decomposition chamber at thermolysis conditions and converting at least a part of the feed stream to acrylic acid;

d. withdrawing a product stream comprising acrylic acid; and

e. recovering at least a portion of the acrylic acid from the product stream wherein the decomposition chamber has an active salt concentration in the range of 0.02 to 10 wt %.

2. The process of claim 1 wherein the feed stream has a polypropiolactone concentration of at least 95 wt %.

3. The process of claim 1 wherein the feed stream has beta-propiolactone concentration of less than 2 wt %.

4. The process of claim 1 wherein the product stream is withdrawn in a vapor phase.

5. The process of claim 1 wherein the active salt is at a concentration in the decomposition chamber in the range of 1 to 5 wt %.

6. The process of claim 5 wherein the feed stream is a liquid and contains the active salt at a concentration in a range of 0.01 to 1 wt %.

7. The process of claim 5 wherein a purge stream comprising active salt is withdrawn from the decomposition chamber at a rate that is adjusted relative to the withdrawal rate of the product stream and input rate of the feed stream to maintain the sodium acrylate concentration in the decomposition chamber within a predetermined range.

8. The process of claim 1 wherein at least one heater directly contacts the feed stream in the decomposition chamber to supply heat to the feed stream contained therein.

9. The process of claim 4 wherein the product stream in vapor phase flows directly from the decomposition chamber into a separation chamber in direct communication with the decomposition chamber for separating acrylic acid from lower boiling materials.

10. The process of claim 1 wherein the decomposition chamber is maintained at a pressure in a range of 1 torr and 5,000 torr and a temperature in range of 100°

C. and 300°

C.

11. The process of claim 1 wherein the feed stream enters the decomposition chamber and the product stream leaves the decomposition chamber at an average residence time in a range of 1 minute to 24 hours.

12. The process of claim 1 wherein the product stream comprises acrylic acid having a concentration in a range of 90% and 99.8% by weight.

13. The process of claim 1 wherein at least a portion of the feed stream is heated prior to entering the decomposition chamber to supply heat to the decomposition vessel.