Systems and processes for producing organic acids directly from beta-lactones

Patent metadata

Field	Value
Publication number	US-12152004-B2
Application number	US-201917054811-A
Country	US
Kind code	B2
Filing date	Jun 25, 2019
Priority date	Mar 21, 2016
Publication date	Nov 26, 2024
Grant date	Nov 26, 2024

Abstract

Provided herein are reactor systems and processes for producing organic acids directly from beta-lactones. Such reactor systems and processes involve the use of a heterogeneous catalyst, such as a zeolite at vapor phase conditions. The reactor systems and processes may use a fixed bed, moving bed or fluidized contacting zone as reactor configurations.

First claim

What is claimed:

1. A process for producing an organic acid directly from a beta-lactone reagent, wherein the beta-lactone reagent is represented by the following formula:

wherein R 1 and R 2 are independently selected from the group consisting of H, alkyl, alkenyl, alkoxy, alkynyl, cycloalkyl, cycloalkenyl and cycloalkynyl, and
wherein both of R 1 and R 2 are not H at the same time,

the method comprising:
introducing the beta-lactone reagent to a reaction vessel;
contacting the beta-lactone reagent with a heterogenous catalyst in the reaction vessel to produce the organic acid; and
removing the organic acid from the reaction vessel, wherein the organic acid is an unsaturated aliphatic carboxylic acid that corresponds to the beta-lactone reagent.

2. The process of claim 1 , wherein the heterogenous catalyst comprises a zeolite.

3. The process of claim 2 , wherein the zeolite catalyst is in a hydrogen form or in metal cation exchanged form.

4. The process of claim 3 , wherein the metal cation is Na + , K + , Ca 2+ , Mg 2+ , Cu 2+ , or Cu + .

5. The process of claim 1 , wherein the organic acid is produced continuously.

6. The process of claim 1 , wherein the beta-lactone reagent is introduced to the reaction vessel combined with a solvent.

7. The process of claim 1 , wherein the reaction vessel further comprises a continuous fixed-bed reactor operating at a pressure between 250 Torr (4.834 psig) and 50 psig.

8. The process of claim 1 , wherein the reaction vessel further comprises a continuous fixed-bed reactor configured for receiving the beta-lactone reagent diluted with inert gas.

9. The process of claim 1 , wherein the least one reaction vessel further comprises a fluidized bed reactor configured to receive the beta-lactone reagent diluted with nitrogen.

10. The process of claim 1 , wherein the least one reaction vessel further comprises a tubular shell-and-tube reactor with a heterogenous catalyst loaded into the tubes and heat transfer fluid fed to the shell side to facilitate temperature control and removal of the heat produced during the reactions.

11. The process of claim 1 , wherein the organic acid is continuously isolated.

12. The process of claim 1 , wherein the organic acid is produced at a yield of at least 50%.

13. The process of claim 1 , wherein the organic acid is produced at a temperature between 100° C. and 300° C.

14. The process of claim 1 , wherein one of R 1 and R 2 is H, and the other of R 1 and R 2 is alkyl.

15. The process of claim 14 , wherein R 1 is alkyl, and R 2 is H.

16. A process for producing an organic acid directly from a beta-lactone reagent, wherein the beta-lactone reagent is a substituted beta-propiolactone represented by the following formula:

wherein R 1 and R 2 are independently selected from the group consisting of H, alkyl, alkenyl, alkoxy, alkynyl, cycloalkyl, cycloalkenyl and cycloalkynyl, and
wherein both of R 1 and R 2 are not H at the same time,

the method comprising:
introducing the beta-lactone reagent to a reaction vessel;
contacting the beta-lactone reagent with a heterogenous catalyst, wherein the heterogenous catalyst is a zeolite, in the reaction vessel to produce the organic acid; and
removing organic acid from the reaction vessel, wherein the organic acid is an unsaturated aliphatic carboxylic acid that corresponds to the substituted beta-propiolactone.

17. The process of claim 16 , wherein the zeolite catalyst is in a hydrogen form or in metal cation exchanged form.

18. The process of claim 16 , wherein the beta-lactone reagent is introduced to the reaction vessel combined with a solvent.

19. The process of claim 16 , wherein the reaction vessel further comprises a continuous fixed-bed reactor configured for receiving the beta-lactone reagent diluted with inert gas.

20. A process for producing an organic acid directly from a beta-lactone reagent, wherein the beta-lactone reagent is a substituted beta-propiolactone represented by the following formula:

wherein R 1 and R 2 are independently selected from the group consisting of H, alkyl, alkenyl, alkoxy, alkynyl, cycloalkyl, cycloalkenyl and cycloalkynyl, and
wherein both of R 1 and R 2 are not H at the same time and one of R 1 and R 2 is H,

the method comprising:
introducing the beta-lactone reagent to a reaction vessel;
contacting the beta-lactone reagent with a heterogenous catalyst, wherein the heterogenous catalyst is a zeolite, in the reaction vessel to produce the organic acid; and
removing organic acid from the reaction vessel, wherein the organic acid is an unsaturated aliphatic carboxylic acid that corresponds to the substituted beta-propiolactone.

Assignees

• Novomer Inc

Inventors

• Sookraj Sadesh H

Classifications

• B01J3/006

  Processes utilising sub-atmospheric pressure; Apparatus therefor · CPC title

• B01J8/067

  Heating or cooling the reactor (B01J8/062 takes precedence) · CPC title

• B01J2219/0004

  Processes in series · CPC title

• C07C67/28

  by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title