IP Library › Granted Patent US 10,087,162
Granted Patent B2
US 10,087,162 · App. 15/525,426 · Granted Oct 2, 2018

Preparation of dialkyl esters of 2,5-furandicarboxylic acid

Inventors: Ana Sofia Vagueiro De Sousa Dias (Amsterdam, NL); Benjamin McKay (Amsterdam, NL); Victor Peter Charles Vreeken (Amsterdam, NL); Gerardus Johannes Maria Gruter (Amsterdam, NL); Johannes Maria Franciscus Sijben (Amsterdam, NL)
Assignee: Synvina C.V.
C07D307/68C07B2200/13
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Quick Facts
Patent No.
US 10,087,162
App. No.
15/525,426
Granted
Oct 2, 2018
Kind
B2
Abstract

Dialkyil esters of 2,5-furandicarboxylic acid are prepared in a process including: contacting an acid starting composition having 2,5-furandicarboxylic acid with an excess of alkanol to form an esterification product having the dialkyil ester of 2,5-furan dicarboxylic acid, water and unreacted alkanol; separating at least part of the unreacted alkanol and water from the esterification product to yield a solid crude product composition having the dialkyil ester of 2,5-furandicarboxylic acid; and subjecting at least part of the solid crude product composition to an evaporation step, where the dialkyil ester of 2,5-furandicarboxylic acid is evaporated and subsequently condensed to yield purified dialkyil ester of 2,5-furandicarboxylic acid.

Claims (19)

1. A process for the preparation of the dialkyl esters of 2,5-furandicarboxylic acid which process comprises:

contacting an acid starting composition comprising 2,5-furandicarboxylic acid with an excess of alkanol to form an esterification product comprising the dialkyl ester of 2,5-furan dicarboxylic acid, water and unreacted alkanol;

separating at least part of the unreacted alkanol and water from the esterification product to yield a solid crude product composition comprising the dialkyl ester of 2,5-furandicarboxylic acid; and

subjecting at least part of the solid crude product composition to an evaporation step, wherein the dialkyl ester of 2,5-furandicarboxylic acid is evaporated and subsequently condensed to yield purified dialkyl ester of 2,5-furandicarboxylic acid,

wherein the solid crude product composition comprising the dialkyl ester of 2,5-furandicarboxylic acid is pre-purified in a concentration zone before being subjected to the evaporation step; and

wherein the evaporation step is conducted in one or more of the equipment selected from a stirrer evaporator, rising film evaporator, circulation evaporator, falling film evaporator and wiped film evaporator.

2. The process according to claim 1 , wherein the evaporation is carried out at a temperature in the range of 120 to 250° C.

3. The process according to claim 1 , wherein the evaporation is carried out at a pressure below 100 mbar.

4. The process according to claim 1 , wherein the contact of 2,5-furandicarboxylic acid with an excess of alkanol is conducted at a temperature of 150 to 300° C., and a pressure of 5 to 25 bar.

5. The process according to claim 1 , wherein the contact of 2,5-furandicarboxylic acid with an excess of alkanol is conducted at a contact time of 0.1 to 3 hr.

6. The process according to claim 1 , wherein the alkanol comprises 1 to 4 carbon atoms.

7. The process according to claim 1 , wherein the 2,5-furandicarboxylic acid and alkanol are contacted in the absence of an esterification catalyst.

8. The process according to claim 1 , wherein the 2,5-furandicarboxylic acid and alkanol are contacted in an esterification zone from which alkanol is continuously withdrawn.

9. The process according to claim 1 , wherein unreacted alkanol from the esterification product is removed by means of distillation, flash distillation or evaporation.

10. The process according to claim 1 , wherein the solid crude product composition is subjected to one or more of the treatments selected from washing, crystallization, re-crystallization and melt crystallization.

11. The process according to claim 1 , wherein the solid crude product composition comprising the dialkyl ester of 2,5-furandicarboxylic acid is washed in a washing zone to yield washed composition comprising the dialkyl ester of 2,5-furan dicarboxylic acid, and the washed composition is crystallized in a crystallization zone to yield crystallized composition that is being subjected to the evaporation step.

12. The process according to claim 1 , which is carried out at as a continuous process.

13. An ester composition comprising dialkyl ester of 2,5-furandicarboxylic acid wherein the composition comprises 99 to 99.9% wt of dialkyl ester of 2,5-furandicarboxylic acid and 1 to 0.1% wt of monoalkyl ester of 2,5-furandicarboxylic acid, the percentages being based on the composition, and which composition has a color of at most 0.005, as measured by absorbance of a 30 mg/L solution in DMSO at a wavelength of 400 nm.

14. The process according to claim 6 , wherein the alkanol is methanol.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2020
From: SYNVINA C.V.
To: FURANIX TECHNOLOGIES B.V.
Reel/Frame 052005/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2017
From: DE SOUSA DIAS, ANA SOFIA VAGUEIRO; MCKAY, BENJAMIN; VREEKEN, VICTOR PETER CHARLES; GRUTER, GERARDUS JOHANNES MARIA; SIJBEN, JOHANNES MARIA FRANCISCUS
To: SYNVINA C.V.
Reel/Frame 043380/0500 →
Priority Claims (1)
NL 2013765 · Nov 10, 2014 · national
Continuity (1)
Related Publication 20170320845A1 · Nov 9, 2017