IP Library Patent Application 15742956
Patent Application
App. No. 15/742,956

PROCESS FOR PRODUCING 2,5-FURANDICARBOXYLIC ACID DIALKYL ESTER

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Patent No.
US None
App. No.
15/742,956
Abstract

Disclosed herein are processes for producing 2,5-furandicarboxylic acid dialkyl ester. In one embodiment, the process comprises a) contacting 2,5-furan dicarboxylic acid, excess alcohol, and optionally, a catalyst in a reactor at a temperature in the range of from 50° C. to 325° C. and a pressure in the range of between 1 bar to 140 bar to form a liquid phase composition comprising an ester of 2,5-furan dicarboxylic acid, the alcohol and water; b) lowering the temperature of the liquid phase composition to form a crude crystallized ester of 2,5-furan dicarboxylic acid; c) separating the product of step b) to form a solids phase comprising a purified ester of 2,5-furan dicarboxylic acid and a mother liquor comprising alcohol and water; and d) removing at least a portion of the water from the mother liquor. In one embodiment, the 2,5-furan dicarboxylic acid is contacted with an alcohol source and optionally, a catalyst.

Claims (24)

1 . A process comprising:

a) contacting 2,5-furan dicarboxylic acid, excess alcohol and, optionally, a catalyst in a reactor at a temperature in the range of from 50° C. to 325° C. and a pressure in the range of between 1 bar to 140 bar to form a liquid phase composition comprising an ester of 2,5-furan dicarboxylic acid, the alcohol and water;

b) lowering the temperature of the liquid phase composition to form a crude crystallized ester of 2,5-furan dicarboxylic acid;

c) separating the product of step b) to form a solids phase comprising a purified ester of 2,5-furan dicarboxylic acid and a mother liquor comprising alcohol and water; and

d) removing at least a portion of the water from the mother liquor.

2 . The process of claim 1 , further comprising step e) distilling the purified ester of 2,5-furan dicarboxylic acid at a temperature in the range of from 38° C. to 204° C. and a pressure in the range of from 0 bar to 3.5 bar.

3 . The process of claim 1 wherein step b) lowering the temperature is conducted in the reactor, in a crystallizing vessel, or in a series of vessels.

4 . The process of claim 1 , wherein in step b) the temperature is in the range of from −5° C. to 50° C.

5 . The process of claim 1 , wherein step d) is performed by one or more steps of

i) distilling the alcohol from the water;

ii) passing the mother liquor through an adsorbent bed;

iii) passing the mother liquor through molecular sieves;

iv) passing the mother liquor through a membrane; or

v) passing the mother liquor through a reverse osmosis system.

6 . The process of claim 1 , wherein the alcohol is methanol.

7 . A process comprising:

a) contacting 2,5-furan dicarboxylic acid, an alcohol source and, optionally, a catalyst in a reactor at a temperature in the range of from 50° to 325° C. and a pressure in the range of from 1 bar to 140 bar to form a liquid composition comprising an ester of 2,5-furan dicarboxylic acid;

b) lowering the temperature of the liquid phase composition to form a crude crystallized ester of 2,5-furan dicarboxylic acid; and

c) separating the product of step b) to form a solids phase comprising a purified ester of 2,5-furan dicarboxylic acid and a mother liquor comprising the alcohol source.

8 . The process of claim 7 , further comprising step d) distilling the purified ester of 2,5-furan dicarboxylic acid at a temperature in the range of from 38° C. to 204° C. and a pressure in the range of from 0 bar to 3.5 bar.

9 . The process of claim 7 , wherein step b) lowering the temperature is conducted in the reactor, in a crystallizing vessel, or in a series of vessels.

10 . The process of claim 7 , wherein in step b) the temperature is in the range of from −5° C. to 50° C.

11 . The process of claim 7 , wherein the alcohol source is an orthoester, an orthoformate, an acetal, an alkyl carbonate, a trialkyl borate, a cyclic ether comprising 3 or 4 atoms in the ring, or a combination thereof.

12 . The process of claim 7 , further comprising a step of recovering at least a portion of the alcohol source from the mother liquor obtained in step c), and optionally recycling the recovered alcohol source to step a).

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ENTITY TYPE PREVIOUSLY RECORDED AT REEL: 049879 FRAME: 0043. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 6, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 050300/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 049879/0043 →