Systems and processes for thermolysis of polylactones to produce organic acids

• US 10,457,624 B2
• Filed: 06/02/2017
• Issued: 10/29/2019
• 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
• Primary Examiner(s): Zucker, Paul A
• Application Number:
  US15/612,884
• Publication Number:
  US 20180305289A1
• Time in Patent Office: 879 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

Reactor systems and processes produce organic acids through thermolysis of polylactones. The reactor systems and processes introduce at least one epoxide reagent and carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet. The epoxide reagent and carbon monoxide reagent contact at least one carbonylation catalyst to produce at least one beta-lactone intermediate. The beta-lactone intermediate is polymerized with at least one initiator in the presence of a metal cation to produce at least one polylactone product. The polylactone product is heated under thermolysis conditions to produce at least one organic acid product. The processes 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 an organic acid product, wherein the process comprises:

a. introducing epoxide reagent and carbon monoxide reagent to a reaction vessel through a feed stream inlet, the reaction vessel comprising a separation chamber positioned above and in direct communication with a thermolysis chamber;

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

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

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

2. The process of claim 1, wherein the epoxide reagent comprises 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, or cyclooctene oxide.

3. The process of claim 1, wherein the epoxide reagent and the carbon reagent enter the reaction vessel with mechanical assistance.

4. The process of claim 1, wherein a mechanical pump assists in introducing the epoxide reagent and the carbon monoxide reagent to the reaction vessel.

5. The process of claim 1, wherein the epoxide reagent and the carbon monoxide reagent are stored at a higher atmospheric pressure than the reaction vessel defining a carbonylation chamber.

6. The process of claim 1, wherein the carbonylation catalyst comprises a metal carbonyl-Lewis acid catalyst.

7. The process of claim 1, wherein the carbonylation catalyst is introduced to the reaction vessel before introducing the carbon monoxide reagent and the epoxide reagent.

8. The process of claim 1, wherein the carbonylation catalyst comprises a neutral metal carbonyl compound.

9. The process of claim 1, wherein the polymerization initiator has a general formula of M″

X where M″

is cationic and X is anionic.

10. The process claim 1, wherein the polymerization initiator comprises a carboxylate salt.

11. The process of claim 1, wherein the polylactone product undergoes thermolysis continuously.