Process for permeation enhanced reactive extraction of levulinic acid

• US 20060201879A1
• Filed: 02/17/2006
• Published: 09/14/2006
• Est. Priority Date: 02/22/2005
• Status: Active Grant

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Haan, Johannes Pieter, Nijmeijer, Arian, Den Boestert, Johannes Leendert Willem Cornelis
• Granted Patent: US 7,501,062 B2
• Time in Patent Office: Days
• US Class Current: 210/634
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 67/58 by liquid-liquid treatment
• CPC Class Codes: C07C 69/716 Esters of keto-carboxylic acids or aldehydo-carboxylic acids

Abstract

A process for permeation enhanced reactive extraction of levulinic acid from a liquid aqueous phase comprising levulinic acid, wherein the levulinic acid from the aqueous phase is brought into contact with a liquid alcohol phase at esterification conditions in the presence of a catalyst at a temperature in the range of from 50 to 250° C., the aqueous phase and the alcohol phase being separated from each other by a membrane, and an aqueous stream depleted in levulinic acid and an alcohol stream comprising ester of levulinic acid are formed.

Claims

1. A process for permeation enhanced reactive extraction of levulinic acid from a liquid aqueous phase comprising levulinic acid, wherein the levulinic acid from the aqueous phase is brought into contact with a liquid alcohol phase at esterification conditions in the presence of a catalyst at a temperature in the range of from 50 to 250°

C., the aqueous phase and the alcohol phase being separated from each other by a membrane, and an aqueous stream depleted in levulinic acid and an alcohol stream comprising ester of levulinic acid are formed.

2. A process according to claim 1, wherein the aqueous phase comprises 1 to 25 wt % of levulinic acid.

3. A process according to claim 1, wherein the alcohol phase comprises at least 90 wt % alcohol.

4. A process according to claim 1, wherein the alcohol phase comprises an alkyl alcohol with at most 12 carbon atoms.

5. A process according to claim 1, wherein the aqueous phase and the alcohol phase are brought into contact with each other in cross-current flow.

6. A process according to claim 1, wherein the ratio of the mass flow of the alcohol phase and the mass flow of the aqueous phase is in the range of from 1:

50 to 1;

2.

7. A process according to claim 1, wherein the catalyst is an acid catalyst.

8. A process according to claim 1, wherein the temperature is in the range of from 60 to 150°

C.

9. A process according to claim 1, wherein the pressure in each of the aqueous phase and the alcohol phase is in the range of from 1 to 30 bar (absolute).

10. A process according to claim 1, wherein the alcohol in the alcohol phase is water-immiscible.

11. A process according to claim 10, wherein the membrane is a porous membrane.

12. A process according to claim 11, wherein the catalyst is present in the aqueous phase.

13. A process according to claim 10, wherein a hydrophilic membrane is used and the alcohol phase has a pressure that is 1 to 10 bar higher than the pressure of the aqueous phase.

14. A process according to claim 1, wherein the alcohol in the alcohol phase is water-miscible.

15. A process according to claim 14, wherein the membrane comprises a hydrophobic membrane layer that is permeable to levulinic acid.

16. A process according to claim 15, wherein the hydrophobic membrane layer is impermeable to water.

17. A process according to claim 15, wherein the hydrophobic membrane layer is a dense layer that is supported on a porous hydrophilic support layer.

18. A process according to claim 15, wherein the catalyst is a heterogeneous catalyst that is located on the membrane surface at the alcohol phase side.

19. A process according to claim 1, wherein the membrane comprises a hydrophobic membrane layer and the aqueous phase has a pressure that is 1 to 10 bar higher than the pressure of the alcohol phase.

20. A process according to claim 1, wherein the alcohol phase comprises ethanol, 1-butanol, 1-pentanol, 1-or 2-hexanol, 2-ethylhexan-1-ol, or 1-decanol.