Production of 5 hydroxymethyulfurfural (HMF) from hexose solutions in the presence of steam

Patent metadata

Field	Value
Publication number	US-9169227-B2
Application number	US-201213711717-A
Country	US
Kind code	B2
Filing date	Dec 12, 2012
Priority date	Dec 13, 2011
Publication date	Oct 27, 2015
Grant date	Oct 27, 2015

Abstract

Method for producing 5-hydroxymethylfurfural (HMF), wherein
a) solutions (hereinbelow called starting solution) which comprise
a hexose and an organic solvent with a boiling point greater than 200° C. (at standard pressure) (for short called high-boiling component), and steam are fed to a reaction vessel,
b) in the reaction vessel, a conversion of the hexose to HMF takes place in the presence of steam with the simultaneous distillative removal of the HMF and c) as distillate, an aqueous, HMF-comprising solution (hereinbelow called distillate) is obtained.

First claim

The invention claimed is:

1. A method for producing 5-hydroxymethylfurfural (HMF), comprising
a) feeding a starting solution which comprises
a hexose and
a high-boiling component which comprises an organic solvent with a boiling point greater than 200° C. (at standard pressure),

 to a reaction vessel,
b) in the reaction vessel, converting the hexose to HMF in the presence of steam with the simultaneous distillative removal of the HMF and
c) obtaining a distillate comprising an aqueous, HMF-comprising solution.

2. The method according to claim 1 , wherein the hexose is fructose, glucose or mixtures of fructose and glucose.

3. The method according to claim 1 , wherein the high-boiling component is a polyether.

4. The method according to claim 3 , wherein the polyether is a poly-C2- to C4-alkylene glycol, the terminal hydroxyl groups of which are optionally etherified with C1-C4 alkyl groups.

5. The method according to claim 1 , wherein the starting solution comprises the high-boiling component in amounts of from 5 to 90% by weight.

6. The method according to claim 1 , wherein the starting solution is an aqueous solution.

7. The method according to claim 1 , wherein the reaction to give HMF takes place in the presence of an acid which is soluble in the starting solution.

8. The method according to claim 1 , wherein the reaction to give HMF takes place at 100° C. to 200° C.

9. The method according to claim 1 , wherein the reaction to give HMF takes place at a pressure of from 1 to 300 mbar.

10. The method according to claim 1 , wherein the method is carried out continuously, where the starting solution and steam are fed to the evaporator continuously and the product solution is drawn off continuously.

11. The method according to claim 1 , wherein the reaction vessel is a thin-film evaporator.

12. The method according to claim 1 , wherein the steam is fed countercurrently to the starting solution.

13. The method according to claim 1 , wherein more than 60% of the HMF obtained are in the distillate.

14. A process comprising:
a) producing HMF by the method according to claim 1 ; and
b) producing 2,5-furandicarboxylic acid or 2,5-bis(hydroxymethyl)furan from the HMF.

15. The method according to claim 1 , wherein the ratio of the volume of steam used in relationship to the volume of starting solution is from 0.5:1 to 2:1.

16. The method according to claim 1 , wherein at least 40% of the hexose is converted to HMF in the method.

17. The method according to claim 1 , further comprising:
d) discharging the steam and the volatile constituents of the starting solution via a separator at the top of an evaporator; and
e) condensing the steam and the volatile constituents to form the distillate.

Assignees

• Basf Se

Inventors

• Backes René
• Blank Benoit
• Kindler Alois
• Feldner Carmen

Classifications

• C07D307/48 Primary

  Furfural · CPC title

• C07D307/46

  Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom · CPC title