Process for the synthesis of 2,5-furandicarboxylic acid

Patent metadata

Field	Value
Publication number	US-9359318-B2
Application number	US-201113814402-A
Country	US
Kind code	B2
Filing date	Aug 4, 2011
Priority date	Aug 6, 2010
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

Process for the synthesis of 2,5-furandicarboxylic acid through the oxidation of -hydroxymethylfurfural in a flow of oxygenor a compound containing oxygen, catalyzed by a supported catalyst containing a metal of the platinum group, carried out in aqueous solution in which the pH is maintained higher than 7 and lower than 12 through the addition of a weak base.

First claim

The invention claimed is:

1. Process for the synthesis of 2,5-furandicarboxylic acid through the oxidation of 5-hydroxymethylfurfural by an oxidising substance which is oxygen or a compound containing oxygen, catalysed by a supported catalyst containing a metal of the platinum group and being free of lead, carried out in aqueous solution whose pH is maintained higher than 7 and lower than 12 through the addition of a weak base, wherein upon completion of the oxidation reaction said catalyst is separated from said aqueous solution and recycled to a new aqueous solution for the synthesis of 2,5-furandicarboxylic acid.

2. Process according to claim 1 wherein the oxidation of 5-hydroxymethylfurfural is carried out by a flow of oxygen.

3. Process according to claim 1 wherein the weak base is added before starting the 5-hydroxymethylfurfural oxidation reaction, wherein the pH value of the aqueous solution containing 5-hydroxymethylfurfural and said weak base is higher than or equal to 8 and lower than 12, and the pH value of the aqueous solution at the end of the oxidation reaction is higher than 7 and lower than 11.

4. Process according to claim 1 wherein part of the weak base is added to the reaction mixture before starting the 5-hydroxymethylfurfural oxidation reaction and part is gradually added after said reaction has started, and wherein the pH of the aqueous solution is maintained higher than 7 and lower than 11.

5. Process according to claim 1 in which the said weak base is selected from: sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, calcium hydroxide, magnesium hydroxide, dibasic and tribasic phosphate buffer solutions and their mixtures.

6. Process according to claim 5 in which the weak base is a poorly soluble weak base.

7. Process according to claim 6 in which said poorly soluble weak base is selected from sodium bicarbonate, calcium and magnesium carbonates, magnesium hydroxides and their mixtures.

8. Process according to claim 1 in which quantities of catalyst metal between 1:60 and 1:500 in moles with respect to 5-hydroxymethylfurfural are used.

9. Process according to claim 1 in which the catalyst is Pt or Pd supported on carbon or alumina.

10. Process according to claim 1 in which the catalyst is recycled at least four times.

11. Process according to claim 1 carried out at a temperature of between 80 and 120° C. and at a pressure of between atmospheric pressure and 10*10 5 Pa.

12. Process according to claim 1 comprising a preliminary stage of oxidising 5-hydroxymethylfurfural catalysed by non-precious metals in order to obtain an easily purifiable reaction intermediate, said intermediate being 5-hydroxymethylfuran-2-carboxylic acid.

13. Process according to claim 1 wherein said 5-hydroxymethylfurfural is obtained from cellulose or polysaccharides containing biomass.

14. Process according to claim 2 wherein the weak base is added before starting the 5-hydroxymethylfurfural oxidation reaction, wherein the pH value of the aqueous solution containing 5-hydroxymethylfurfural and said weak base is higher than or equal to 8 and lower than 12, and the pH value of the aqueous solution at the end of the oxidation reaction is higher than 7 and lower than 11.

15. Process according to claim 2 wherein part of the weak base is added to the reaction mixture before starting the 5-hydroxymethylfurfural oxidation reaction and part is gradually added after said reaction has started, and wherein the pH of the aqueous solution is maintained higher than 7 and lower than 11.

16. Process according to claim 2 in which the said weak base is selected from: sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, calcium hydroxide, magnesium hydroxide, dibasic and tribasic phosphate buffer solutions and their mixtures.

17. Process according to claim 3 in which the said weak base is selected from: sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, calcium hydroxide, magnesium hydroxide, dibasic and tribasic phosphate buffer solutions and their mixtures.

18. Process according to claim 4 in which the said weak base is selected from: sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, calcium hydroxide, magnesium hydroxide, dibasic and tribasic phosphate buffer solutions and their mixtures.

19. Process according to claim 2 in which quantities of catalyst metal between 1:60 and 1:500 in moles with respect to 5-hydroxymethylfurfural are used.

20. Process according to claim 1 wherein said catalyst consists of said metal of the platinum group.

Assignees

• Borsotti Giampietro
• Digioia Francesca
• Novamont Spa

Inventors

• Borsotti Giampietro
• Digioia Francesca

Classifications

• C07D307/30 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D307/24

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C07D307/68 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C07D307/48

  Furfural · CPC title

• B01J23/40

  of the platinum group metals · CPC title