Method for preparing a polyester under specific esterification conditions

Patent metadata

Field	Value
Publication number	US-9840582-B2
Application number	US-201515122960-A
Country	US
Kind code	B2
Filing date	Mar 11, 2015
Priority date	Mar 11, 2014
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

A polyester including poly(ethylene 2,5-furandicarboxylate is prepared by esterification of a starting mixture including 2,5-furandicarboxylic acid and ethylene glycol to form an ester composition, and by subjecting the ester composition thus obtained to polycondensation at reduced pressure in the presence of a polycondensation catalyst to obtain a polycondensate. The mixture is reacted under conditions such that the esterification potential as defined by Esterification Potential (EsPo)=(MR−1) 2 *P H2O (T), where MR represents the molar ratio of ethylene glycol over 2,5-furandicarboxylic acid, MR being greater than 1; P H2O (T) represents the pure component vapor pressure (in bar) of water at temperature T, which is the final reaction temperature in the esterification mixture before the pressure is reduced to effect the polycondensation, is less than 0.8.

First claim

The invention claimed is:

1. A method for the preparation of a polyester, wherein a starting mixture comprising 2,5-furandicarboxylic acid and ethylene glycol is subjected to esterification to form an ester composition, and the ester composition thus obtained is subjected to polycondensation at reduced pressure in the presence of a polycondensation catalyst to obtain a polycondensate,
wherein 2,5-furandicarboxylic acid and ethylene glycol are reacted under conditions such that the esterification potential as defined by
Esterification Potential (EsPo)=(MR−1) 2 *P H2O ( T ),

wherein MR represents the molar ratio of ethylene glycol over 2,5-furandicarboxylic acid, MR being greater than 1;
P H2O (T) represents the pure component vapor pressure (in bar) of water at temperature T, which is the final reaction temperature in the esterification mixture before the pressure is reduced to effect the polycondensation, is less than 0.8.

2. The method according to claim 1 wherein the esterification potential is at least 0.03.

3. The method according to claim 1 , wherein the molar ratio of 2,5-furandicarboxylic acid to ethylene glycol MR in the starting mixture is 1:1.01 to 1:1.15.

4. The method according to claim 1 , wherein the esterification reaction between 2,5-furandicarboxylic acid and ethylene glycol is carried out at a temperature of 160 to 240° C. and a pressure of 0.9 to 5 bar for a period of 0.5 to 4 hr.

5. The method according to claim 1 , wherein the polycondensation step is carried out in the presence of a polycondensation catalyst selected from the catalysts comprising one or more elements selected from tin, zinc, titanium, antimony.

6. The method according to claim 5 , wherein the polycondensation catalyst is added to the starting mixture of 2,5-furandicarboxylic acid and ethylene glycol.

7. The method according to claim 1 , wherein the polycondensation comprises a pre-polycondensation reaction and a polycondensation reaction.

8. The method according to claim 7 , wherein the pre-polycondensation reaction is conducted at a temperature of 180 to 240° C. and a pressure of 20 to 700 mbar.

9. The method according to claim 7 , wherein the polycondensation reaction is carried out at a temperature of 245 to 270° C. and a pressure of 0.05 to 5 mbar.

10. The method according to claim 1 , wherein the polycondensation is carried out for a time sufficient to achieve a polyester with an IV of 0.45 dL/g or higher.

11. The method according to claim 10 , wherein the polyester has an IV of 1.0 dL/g or less.

12. The method according to claim 1 , wherein at least a portion of the polycondensation reaction is conducted in a disc-type or cage-type reactor.

13. The method according to claim 1 , wherein the polycondensate obtained is subjected to a pelletizing step, such that solid particles are obtained.

14. The method according to claim 1 , wherein the polycondensate is crystallized at a temperature in the range of 90 to 200° C.

15. The method according to claim 1 , wherein the polycondensate obtained is subjected to solid state polymerization.

Assignees

• Furanix Technologies Bv

Inventors

• Kolstad Jeffrey John
• Dam Matheus Adrianus
• Wang Bing
• Schiavone Robert Joseph
• Andrews Marion L
• Paschke Edward E

Classifications

• C08G63/80 Primary

  Solid-state polycondensation · CPC title

• C08G63/866

  Antimony or compounds thereof · CPC title

• C08G63/78 Primary

  Preparation processes · CPC title

• C08G63/16

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G63/181 Primary

  Acids containing aromatic rings · CPC title