Simultaneous recovery of organic compounds and extractants

Patent metadata

Field	Value
Publication number	US-10265641-B2
Application number	US-201515306932-A
Country	US
Kind code	B2
Filing date	May 1, 2015
Priority date	May 1, 2014
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

The invention relates to a method for recovering an organic compound from a feed stream comprising the steps of —extracting the organic compound into an organic solvent, thereby obtaining a mixture of the solvent and the organic compound; and —simultaneously crystallizing the solvent and the organic compound by cooling the mixture; and —separating the solid organic solvent and solid organic compound.

First claim

The invention claimed is:

1. Method for recovering an organic compound from a liquid feed stream comprising the steps of:
a liquid-liquid extraction, wherein the organic compound is extracted from the feed stream into an organic solvent, thereby obtaining an extract, which is a mixture of the organic solvent and the organic compound;
simultaneously crystallizing the solvent and the organic compound by cooling said mixture; and
a solid-solid separation step to separate the solid solvent and solid organic compound, wherein the organic compound is selected from the group consisting of carboxylic acids, alcohols and cyclic esters.

2. Method according to claim 1 , wherein the solid solvent and solid organic compound are separated based on their difference in density or size.

3. Method according to claim 1 , wherein the solid solvent and solid organic compound are separated by gravity settling, flotation, hydrocyclones, or centrifugation.

4. Method according to claim 1 , wherein the solvent and the organic compound are simultaneously crystallized by cooling the mixture to a temperature equal to or lower than the eutectic temperature of the mixture.

5. Method according to claim 1 , wherein the organic compound is selected from the group consisting of 1,4-butanediol, succinic acid, formic acid, malic acid, 2,5-furan dicarboxylic acid, 3-hydroxypropionic acid, aspartic acid, glucaric acid, glutamic acid, itaconic acid, levulinic acid, 3-hydroxybutyrolactone, glycerol, sorbitol, xylitol and arabitol.

6. Method according to claim 1 , wherein the organic solvent has a melting point in the range of +10 to +100° C.

7. Method according to claim 1 , wherein the organic solvent is selected from the group consisting of trialkylphosphine oxides, dialkylsulfoxides, aliphatic hydrocarbons, aromatic hydrocarbons, alcohols, carboxylic acids and esters.

8. Method according to claim 1 , wherein the mixture has a eutectic temperature in the range of −20 to +80° C.

9. Method according to claim 1 , wherein the stream is a fermentation stream.

10. Method according to claim 1 , wherein the method further comprises the step of fermenting a carbon source to obtain the organic compound.

11. Method according to claim 1 , wherein the liquid feed stream is an aqueous stream.

12. Method according to claim 1 , wherein the organic compound is 1,4-butanediol or itaconic acid; and wherein the organic solvent is tri-n-octylphosphine oxide.

13. Mixture comprising at least 1 wt. % crystals of a first organic compound, at least 1 wt. % crystals of a second organic compound different than the first compound and at least 25 wt. % of the first or second organic compound in liquid form, based on the total weight of the mixture.

14. Mixture obtainable by the simultaneous crystallization step as defined in claim 1 .

15. Mixture according to claim 13 , wherein the combined amount of crystals of the first and second organic compound is 10-50 wt. %, based on the total weight of the mixture.

16. Mixture according to claim 13 , wherein the first compound is 1,4-butanediol or itaconic acid; and wherein the second compound is tri-n-octylphosphine oxide.

17. Method for recovering an organic compound from a liquid feed stream comprising the steps of:
a liquid-liquid extraction, wherein the organic compound is extracted from the feed stream into an organic solvent, thereby obtaining an extract, which is a mixture of the organic solvent and the organic compound;
simultaneously crystallizing the solvent and the organic compound by cooling said mixture; and
a solid-solid separation step to separate the solid solvent and solid organic compound, wherein the organic solvent is a trialkylphosphine oxide or dialkylsulfoxide.

18. Method according to claim 17 , wherein the solid solvent and solid organic compound are separated based on their difference in density or size.

19. Method according to claim 17 , wherein the solid solvent and solid organic compound are separated by gravity settling, flotation, hydrocyclones, or centrifugation.

20. Method according to claim 17 , wherein the solvent and the organic compound are simultaneously crystallized by cooling the mixture to a temperature equal to or lower than the eutectic temperature of the mixture.

21. Method according to claim 17 , wherein the organic compound has a melting point in the range of −50 to +250° C.

22. Method according to claim 17 , wherein the organic solvent is selected from tri-n-octylphosphine oxide (TOPO), dimethylsulfoxide (DMSO), and dibutylsulfoxide (DBSO).

23. Method according to claim 17 , wherein the mixture has a eutectic temperature in the range of −20 to +80° C.

24. Method according to claim 17 , wherein the stream is a fermentation stream.

25. Method according to claim 17 , wherein the method further comprises the step of fermenting a carbon source to obtain the organic compound.

26. Method according to claim 17 , wherein the liquid feed stream is an aqueous stream.

Assignees

• TNO

Inventors

• Roa Engel Carol Andrea
• Urbanus Jan Harm
• Verdoes Dirk

Classifications

• B01D9/04 Primary

  concentrating solutions by removing frozen solvent therefrom · CPC title

• C12P7/18

  polyhydric · CPC title

• C07F9/5095

  Separation; Purification; Stabilisation · CPC title

• C07C51/42

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C51/43

  by change of the physical state, e.g. crystallisation · CPC title