Process for purifying an acid composition comprising 2-formyl-furan-5-carboxylic acid and 2,5-furandicarboxylic acid

Patent metadata

Field	Value
Publication number	US-2016207898-A1
Application number	US-201414914972-A
Country	US
Kind code	A1
Filing date	Aug 29, 2014
Priority date	Aug 30, 2013
Publication date	Jul 21, 2016
Grant date	—

Abstract

An acid composition comprising 2-formyl-furan-5-carboxylic acid and 2,5-furandicarboxylic acid is purified in a process which comprises; contacting the acid composition with an alcohol to obtain an esterified composition; and separating the ester of 2-formyl-furan-5-carboxylic acid from the esterified composition to obtain a purified esterified product; and contacting the purified esterified composition with water for saponification or hydrolysis, to obtain a product composition, comprising 2,5-furandicarboxylic acid and a reduced amount of 2-formyl-furan-5-carboxylic acid.

First claim

1 . A process for purifying an acid composition comprising 2-formyl-furan-5-carboxylic acid and 2,5-furandicarboxylic acid, which process comprises the steps of:
contacting the acid composition with an alcohol to obtain an esterified composition; separating the ester of 2-formyl-furan-5-carboxylic acid from the esterified composition to obtain a purified esterified product; and contacting the purified esterified composition with water for saponification or hydrolysis, to obtain a product composition, comprising 2,5-furandicarboxylic acid and a reduced amount of 2-formyl-furan-5-carboxylic acid.

2 . The process according to claim 1 , wherein the acid composition originates from the oxidation of 5-alkoxymethylfurfural, 5-hydroxymethylfurfural or a mixture thereof.

3 . The process according to claim 1 , wherein the acid composition comprises from 0.1 to 4.0% wt of 2-formyl-furan-5-carboxylic acid, based on the weight of the acid composition.

4 . The process according to claim 1 , wherein the acid composition is contacted with a mono-alcohol.

5 . The process according to claim 4 , wherein the mono-alcohol is an alkanol having from 1 to 8 carbon atoms.

6 . The process according to claim 1 , wherein the alcohol is present in a molar excess of the acid composition.

7 . The process according to claim 1 , wherein the acid composition is contacted with an alcohol in the presence of an esterification catalyst.

8 . The process according to claim 1 , wherein the acid composition is contacted with an alcohol in the absence of an esterification catalyst.

9 . The process according to claim 7 , wherein the esterification catalyst is an acid catalyst, the acid catalyst being selected from the group consisting of mineral inorganic acids, zeolites, ion exchange resins and mixtures thereof.

10 . The process according to claim 1 , wherein the acid composition is contacted with an alcohol at a temperature of 60 to 250° C. and a pressure of 1 to 100 bar.

11 . The process according to claim 1 , wherein the esterified composition is subjected to crystallization and/or distillation.

12 . The process according to claim 11 , wherein the esterified composition is allowed to crystallize by cooling the esterified composition to a temperature of −30 to 40° C.

13 . The process according to claim 12 , wherein the purified esterified composition is allowed to crystallize by cooling the esterified composition to a temperature of −10 to 30° C.

14 . The process according to claim 1 , wherein the purified esterified composition is contacted with water in the presence of a hydrolysis catalyst.

15 . The process according to claim 1 , wherein the purified esterified composition is contacted with water in the absence of a hydrolysis catalyst.

16 . The process according to claim 1 , wherein the purified esterified composition is contacted with water at a temperature of 120 to 180° C. and a pressure of 5 to 30 bar.

17 . The process according to claim 1 , which is conducted as a continuous process.

18 . The process according to claim 4 , wherein the mono-alcohol is an alkanol having from 1 to 8 carbon atoms, the alkanol being ethanol or methanol.

19 . The process according to claim 1 , wherein the alcohol is present in a molar excess of the acid composition, the molar ratio between alcohol and the acid composition being from 5:1 to 100:1.

20 . The process according to claim 1 , wherein the acid composition is contacted with an alcohol at a temperature of 70 to 200° C. and a pressure of 1 to 70 bar.

Assignees

• Furanix Technologies Bv

Inventors

• Singh Jagdeep
• Mckay Benjamin
• Wang Bing
• Dam Matheus Adrianus
• Gruter Gerardus Johannes Maria
• De Sousa Dias Ana Sofia Vagueiro

Classifications

• C07B63/02 Primary

  by treatment giving rise to a chemical modification · CPC title

• C07D307/68 Primary

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

• B01J31/08

  Ion-exchange resins · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• B01J29/00

  Catalysts comprising molecular sieves {(molecular sieves per se C01B)} · CPC title