SYSTEMS AND PROCESSES FOR THERMOLYSIS OF POLYLACTONES TO PRODUCE ORGANIC ACIDS

• US 20180305289A1
• Filed: 06/02/2017
• Published: 10/25/2018
• Est. Priority Date: 04/24/2017
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H., Sherry, Kyle Evan
• Granted Patent: US 10,457,624 B2
• Time in Patent Office: 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 systems and processes for producing organic acids through thermolysis of polylactones. In preferred embodiments, the reactor systems and processes are capable of introducing at least one epoxide reagent and carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet; contacting the at least one epoxide reagent and carbon monoxide reagent with at least one carbonylation catalyst to produce at least one beta-lactone intermediate; polymerizing the at least one beta-lactone intermediate with at least one initiator in the presence of a metal cation to produce at least one polylactone product; and heating the at least one polylactone product under thermolysis conditions to produce at least one organic acid product. Advantageously, the processes of the present invention may control the presence of contaminates, impurities, catalytic materials, and/or reagents to provide for highly pure organic acid products.

Claims

1. A process for producing at least one organic acid product, wherein the process comprises the steps for:

a. introducing at least one polylactone product to a reaction vessel through a feed stream inlet; and

b. heating the at least one polylactone product under thermolysis conditions to produce at least one organic acid product.

2. A process for producing at least one organic acid product, wherein the process comprises the steps for:

a. introducing at least one epoxide reagent and carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet;

b. contacting the at least one epoxide reagent and carbon monoxide reagent with at least one carbonylation catalyst to produce at least one beta-lactone intermediate;

c. polymerizing the at least one beta-lactone intermediate with at least one initiator in the presence of a metal cation to produce at least one polylactone product; and

d. heating the at least one polylactone product under thermolysis conditions to produce the at least one organic acid product.

3. The process for producing at least one organic acid product from claim 2, wherein the at least one epoxide reagent is chosen from the group comprising ethylene oxide, propylene oxide, 1,2-epoxyhexane, 1,2-epoxydodecane, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, 1,2-epoxy-9-decene, isoprene monoxide, epichlorohydrin, 1,3-butadiene diepoxide, 1,2,7,8-diepoxyoctane, 1,2-epoxycyclopentane, and cyclooctene oxide.

4. The process for producing at least one organic acid product from claim 2, wherein the at least one epoxide reagent and at least one carbon reagent may enter the at least one reaction vessel with mechanical assistance.

5. The process for producing at least one organic acid product from claim 2, wherein a mechanical pump may assist in introducing the at least one epoxide reagent and at least one carbon reagent to the at least one reaction vessel.

6. The process for producing at least one organic acid product from claim 2, wherein the at least one epoxide reagent and at least one carbon monoxide reagent may be stored at a higher atmospheric pressure than at least one reaction vessel defining a carbonylation chamber.

7. The process for producing at least one organic acid product from claim 2, wherein the carbonylation catalyst includes at least one metal carbonyl-Lewis acid catalyst.

8. The process for producing at least one organic acid product from claim 2, wherein the carbonylation catalyst is introduced to the at least one reaction vessel before introducing the at least one carbon monoxide reagent or at least one epoxide reagent.

9. The process for producing at least one organic acid product from claim 2, wherein the carbonylation catalyst includes a neutral metal carbonyl compound.

10. The process for producing at least one organic acid product from claim 2, wherein the polymerization initiator is an ionic initiator having the general formula of M″

X where M″

is cationic and X is anionic.

11. The process for producing at least one organic acid product from claim 2, wherein the polymerization initiator comprises a carboxylate salt.

12. The process for producing at least one organic acid product from claim 2, wherein at least one polylactone product undergoes thermolysis continuously.

14. The reactor system for producing at least one organic acid product from claim 12, wherein the system includes at least one motor driven mixing blade.

15. The reactor system for producing at least one organic acid product from claim 12, wherein the system includes at least one jet mixer.

16. The reactor system for producing at least one organic acid product from claim 12, wherein said heater comprises at least one heat exchange surface in the at least one reaction vessel.

17. The reactor system for producing at least one organic acid product from claim 12, wherein the system includes at least one reaction vessel which defines a slipstream outlet.

13. A reactor system for producing at least one organic acid product comprising:

a. at least one reaction vessel defining a thermolysis chamber sized and shaped to define an interior volume and a retaining volume within a lower portion of said interior volume wherein said retaining volume is suitable to retain at least one polylactone product in a liquid or semiliquid state;

b. at least one feed stream inlet defined by said at least one reaction vessel and adapted for feeding the at least one polylactone product into said thermolysis chamber;

c. at least one heater adapted to supply heat to a liquid or semiliquid retained in the at least one reaction vessel;

d. a separation chamber defined by said at least one reaction vessel and positioned above and in direct communication with said thermolysis chamber; and

e. at least one product outlet defined by said at least one reaction vessel and in direct communication with said separation chamber suitable for withdrawing a product stream comprising at least one organic acid products.

18. A reactor system for producing at least one organic acid product comprising:

a. at least one reaction vessel defining a polymerization chamber for use in performing a step for polymerizing at least one beta-lactone intermediate with at least one initiator in the presence of a metal cation to produce at least one polylactone product; and

b. at least one reaction vessel defining a thermolysis chamber for use in performing a step for heating the at least one polylactone product under thermolysis conditions to produce at least one organic acid product.

19. The reactor system for producing at least one organic acid product from claim 18, wherein the system includes a bottoms squeezer in communication with said slipstream outlet.

20. The reactor system for producing at least one organic acid product from claim 18, wherein the system includes at least one recycle stream.

21. The reactor system for producing at least one organic acid product from claim 18, wherein the system includes at least one reaction vessel defining a carbonylation chamber for use in performing a step for contacting the at least one epoxide reagents and carbon monoxide reagents with at least one carbonylation catalyst to produce at least one beta-lactone intermediate.

22. The reactor system for producing at least one organic acid product from claim 18, wherein said at least one reaction vessel defining a polymerization chamber is at least 10 miles from said at least one reaction vessel defining a thermolysis chamber.

23. The reactor system for producing at least one organic acid product from claim 18, wherein said at least one reaction vessel defining a polymerization chamber is at least 100 miles from said at least one reaction vessel defining a thermolysis chamber.

24. The reactor system for producing at least one organic acid product from claim 18, wherein the system includes a heat transfer medium for directing heat produced from said at least one reaction vessel defining a polymerization chamber to said at least one reaction vessel defining a thermolysis chamber.

25. The reactor system for producing at least one organic acid product from claim 21, wherein the system includes a heat transfer medium for directing heat produced from said at least one reaction vessels defining a carbonylation chamber to said at least one reaction vessel defining a thermolysis chamber.