Systems and Processes for Producing Organic Acids Direct from Beta-Lactones

• US 20180305286A1
• Filed: 06/29/2018
• Published: 10/25/2018
• Est. Priority Date: 03/21/2016
• Status: Abandoned Application

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H.
• Application Number:
  US16/023,410
• Publication Number:
  US 20180305286A1
• Time in Patent Office: Days
• CPC Class Codes: B01J 2219/0004 Processes in series
• CPC Class Codes: B01J 3/006 Processes utilising sub-atmospheric pressure; Apparatus therefor
• CPC Class Codes: B01J 8/067 Heating or cooling the reactor B01J8/062 takes precedence
• CPC Class Codes: C07C 231/12 by reactions not involving the formation of carboxamide groups
• CPC Class Codes: C07C 309/22 containing carboxyl groups bound to the carbon skeleton
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C07C 57/08 Crotonic acid
• CPC Class Codes: C07C 57/13 Dicarboxylic acids
• CPC Class Codes: C07C 57/52 containing halogen
• CPC Class Codes: C07C 59/42 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 59/58 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 59/62 containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 59/68 the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 67/28 by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
• CPC Class Codes: C07C 69/145 of unsaturated alcohols
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C07C 69/593 Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C07C 69/78 Benzoic acid esters
• CPC Class Codes: C07D 307/54 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 317/30 : Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07F 7/1804 : Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 7/1892 : by reactions not provided for in C07F7/1876 - C07F7/1888
• CPC Class Codes: Y02P 20/582 : Recycling of unreacted starting or intermediate materials

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.

Claims

1. A process for producing at least one organic acid product directly from at least one beta-lactone reagent, wherein the at least one beta-lactone reagent is represented by the following formula:

2. The process from claim 1, wherein the heterogenous catalyst comprises a microporous solid selected from the group including alkaline-earth phosphates, supported phosphate salts, calcium hydroxyapatites, inorganic salts, metal oxides, and zeolites, or combinations thereof.

3. The process from claim 1, wherein the heterogenous catalyst comprises an alumina-silicate molecular sieve having Lewis or Brö

nsted acidity.

4. The process from claim 1, wherein the heterogenous catalyst comprises a zeolite.

5. The process from claim 4, wherein the heterogenous catalyst comprises Zeolite Y, beta Zeolite, ZSM-5, ZSM-11 ZSM-22, MCM-22, ZSM-35, Zeolite A, or combinations thereof.

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

7. The process from claim 6, wherein the metal cations are Na⁺, K⁺, Ca²⁺, Mg²⁺, Cu²⁺, Cu⁺.

8. The process from claim 1, wherein the at least one organic acid product is produced continuously.

9. The process from claim 1, wherein the at least one beta-lactone reagent is introduced to the at least one reaction vessel combined with a solvent.

10. The process from claim 1, wherein the at least one reaction vessel further comprises a continuous fixed-bed reactor operating at a reduced pressure.

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

12. The process from claim 1, wherein the least one reaction vessel further comprises a fluidized bed reactor configured to receive at least one beta-lactone reagent diluted with inert gas such as nitrogen.

13. The process from 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.

14. The process from claim 1, wherein the beta-lactone reagent is provided at a weight hourly space velocity of 0.1 h⁻

1 to 2.1 h<sup>−

1</sup>.

15. The process from claim 1, wherein the beta-lactone reagent is provided at a weight hourly space velocity of 0.3 h-1 to 0.9 h-1.

16. The process from claim 1, wherein the at least one organic acid product is continuously isolated.

17. The process from claim 1, wherein the at least one organic acid product is produced at a yield of at least 50%.

18. The process from claim 1, wherein the at least one organic acid product is produced at a temperature between 100°

C. and 300°

C.

19. A reactor system for producing at least one organic acid product directly from at least one beta-lactone reagent, wherein the at least one beta-lactone reagent is represented by the following formula:

20. The reactor from claim 19, wherein the at least one reaction vessel further comprises a fixed-bed reactor.

21. The reactor system from claim 19, wherein the at least one reaction vessel further comprises a continuous fixed-bed reactor operating at a reduced pressure for production of at least one organic acid product.

22. The reactor system from claim 19, wherein the at least one reaction vessel further comprises a continuous fixed-bed reactor configured for receiving at least one beta-lactone reagent diluted with inert solvent or gas.

23. The reactor system from claim 19, wherein the at least one reaction vessel further comprises a fluidized bed reactor configured to receive at least one beta-lactone reagent diluted with inert gas.

24. The reactor system from claim 19, wherein the at least one reaction vessel further comprises two or more sections separated by one or more heaters.

25. The reactor system from claim 19, wherein the at 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.

26. The reactor system from claim 19, wherein the at least one reaction vessel further comprises a regeneration vessel for the regeneration of at least one heterogenous catalyst.