Conversion and purification of biomass

Patent metadata

Field	Value
Publication number	US-2016207899-A1
Application number	US-201415023668-A
Country	US
Kind code	A1
Filing date	Sep 17, 2014
Priority date	Sep 20, 2013
Publication date	Jul 21, 2016
Grant date	—

Abstract

The present invention relates to a method for synthesizing an optionally substituted furoic acid by dehydrating a biomass and oxidizing the optionally substituted furan derived from the dehydration reaction. Water extraction has been incorporated as a step between the dehydration and the oxidation in order to purify the intermediate optionally substituted furan before having it oxidized. Prior to this water extraction, the organic solvent used for dehydration may be separated by evaporation. The provision of the water extraction allows impurities to be separated from the intermediate optionally substituted furan.

First claim

1 . A method for synthesizing an optionally substituted furoic acid, comprising:
converting a biomass to an optionally substituted furan, wherein said furan is unsubstituted or substituted by at least one —C 1 -C 10 -alkyl-OH group, via a dehydration reaction in the presence of an organic solvent; purifying the optionally substituted furan by first evaporating the organic solvent from the optionally substituted furan produced from said dehydration reaction to obtain a solid residue or an aqueous slurry, followed by adding water to the residue or aqueous slurry for extraction of the optionally substituted furan with water, collecting the supernatant separately from the residue; and oxidizing the extracted optionally substituted furan to form the optionally substituted furoic acid.

2 . The method according to claim 1 , wherein the water extraction is repeated several times and the extracts containing the optionally substituted furan are combined, preferably wherein said water extraction is repeated for 2 to 3 times.

3 . (canceled)

4 . The method according to claim 1 , wherein said dehydration reaction is an acid catalyzed dehydration reaction, preferably wherein said acid catalyzed dehydration reaction occurs in the presence of a mono-phase solvent system or a biphasic solvent system.

5 . (canceled)

6 . The method according to claim 1 , wherein said optionally substituted furan is 5-(hydroxymethyl)furfural.

7 . The method according to claim 1 , wherein said organic solvent is selected from the group consisting of alcohols, ketones, tetrahydrofuran, γ-valerolactone or mixtures thereof.

8 . The method according to claim 7 , wherein the organic solvent is selected from isopropanol, 1-butanol or methyl isobutyl ketone, preferably wherein said organic solvent is isopropanol.

9 . (canceled)

10 . The method according to claim 7 which comprises an ionic liquid as the co-solvent used in the dehydration reaction, preferably wherein said ionic liquid is water.

11 . (canceled)

12 . The method according to claim 1 , wherein the oxidization of the optionally substituted furan is carried out in the presence of oxygen, a catalytic system and optionally a base.

13 . The method according to claim 12 , wherein said catalytic system is a supported catalytic system comprising gold/hydrotalcite, gold-palladium/hydrotalcite or platinum/carbon.

14 . The method according to claim 12 , wherein said catalytic oxidation is carried out for about 1 to 3 hours at about 30 to 70° C.

15 . The method according to claim 12 , wherein said catalytic oxidation is further carried out for 4 to 10 hours at 80 to 110° C.

16 . The method according to claim 1 , wherein said biomass is Jerusalem artichoke.

17 . The method according to claim 1 , wherein said biomass comprises a carbohydrate, preferably wherein said carbohydrate is selected from cellulose, fructose, glucose or any other sugar.

18 . (canceled)

19 . The method according to claim 1 , wherein said optionally substituted furoic acid is 2,5-furandicarboxylic acid.

20 . The method according to claim 1 , wherein said optionally substituted furoic acid is 5-hydroxymethyl-2-furancarboxylic acid.

21 . An aqueous solution of 5-(hydroxymethyl)furfural obtained by:
converting a biomass to an optionally substituted furan, wherein said furan is unsubstituted or substituted by at least one —C 1 -C 10 -alkyl-OH group, via a dehydration reaction in the presence of an organic solvent; purifying the optionally substituted furan by evaporating the organic solvent from the optionally substituted furan produced from said dehydration reaction to obtain a solid residue or an aqueous slurry, followed by adding water to the residue or aqueous slurry for extraction of the optionally substituted furan with water and collecting the supernatant separately from the residue.

22 . The aqueous solution according to claim 21 , wherein the water extraction is repeated several times and the extracts containing the optionally substituted furan are combined.

23 . Use of an aqueous solution of 5-(hydroxymethyl)furfural obtained by:
converting a biomass to an optionally substituted furan, wherein said furan is unsubstituted or substituted by at least one —C 1 -C 10 -alkyl-OH group, via a dehydration reaction in the presence of an organic solvent; purifying the optionally substituted furan by evaporating the organic solvent from the optionally substituted furan produced from said dehydration reaction to obtain a solid residue or an aqueous slurry, followed by adding water to the residue or aqueous slurry for extraction of the optionally substituted furan with water and collecting the supernatant separately from the residue, to convert 5-(hydroxymethyl) furfural to 2,5-furandicarboxylic acid by catalytic oxidation.

24 . The use according to claim 23 , wherein said catalytic oxidation is carried out in the presence of oxygen, a catalytic system and optionally a base.

25 . The use according to claim 24 , wherein said catalytic system is a supported catalytic system comprising gold/hydrotalcite, gold-palladium/hydrotalcite or platinum/carbon.

Assignees

• Agency Science Tech & Res

Inventors

• Yi Guangshun
• Zhang Yugen

Classifications

• B01J35/45

  Nanoparticles · CPC title

• C07D307/68 Primary

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

• B01J35/0013

  Operations & Transport · mapped topic

• B01J23/52

  Gold · CPC title

• B01J23/007

  Mixed salts · CPC title