Production of purified dialkyl-furan-2,5-dicarboxylate (dafd) in a retrofitted dmt plant

Patent metadata

Field	Value
Publication number	US-2020002301-A1
Application number	US-201916562537-A
Country	US
Kind code	A1
Filing date	Sep 6, 2019
Priority date	Jul 20, 2017
Publication date	Jan 2, 2020
Grant date	—

Abstract

Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.

First claim

What we claim is:

1 . A process for the manufacture of a DAFD vapor comprising:
a) feeding a composition comprising furan-2,5-dicarboxylic acid (“FDCA”) in an amount greater than 90wt % to an esterification reaction zone; and b) in the presence of an alcohol compound, conducting an esterification reaction in the esterification reaction zone to react FDCA with said alcohol compound to form a crude diester composition comprising dialkyl furan-2,5-dicarboxylate (“DAFD”), the alcohol compound, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), alkyl furan-2-carboxylate (AFC), and alkyl-5-formylfuran-2-carboxylate (AFFC); and wherein said esterification reactor zone comprises at least one reactor, wherein said reactor has been previously used in an DMT(dimethyl terephthalate) process; and wherein the process for the oxidation of the oxidizable material containing the furan group can be integrated with the process for the manufacture of the diester composition; and wherein an integrated process includes co-locating the two manufacturing facilities, one for oxidation and the other for esterification, within 10 miles.

2 . The process according to claim 1 further comprising
c) separating at least a portion of the alcohol compound from the crude diester composition in a flash zone using a physical separation process to produce:
(i) a vapor alcohol composition, comprising said alcohol compound, taken as an overhead stream that is rich in the concentration of alcohol, relative to the alcohol concentration in the crude diester composition feeding the flash zone, and (ii) a first liquid DAFD rich composition, comprising DAFD, ACFC, AFC, and AFFC, that is rich in the total concentration of DAFD relative to the total concentration of DAFD in the crude diester composition feeding the flash zone; and
separating at least a portion of DAFD from the first liquid DAFD rich composition in a product recovery zone;

wherein the process produces:
(i) a purified DAFD vapor composition rich in the concentration of DAFD relative to the concentration of DAFD in the first liquid DAFD rich composition; and
(ii) a liquid ACFC composition that is rich in the concentration of ACFC relative to the concentration of ACFC in the first liquid DAFD rich composition;
(iii) a vapor AFC composition comprising AFC that is rich in the concentration of AFC relative to the concentration of AFC in the first liquid DAFD rich composition; and
(iv) a second alcohol composition comprising alcohol that is rich in the concentration of alcohol, relative to the first liquid DAFD rich composition.

3 . The process of claim 2 , wherein the alcohol comprises methanol, the DAFD comprises dimethyl-furan-2,5-dicarboxylate (“DMFD”), the ACFC comprises 5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC), the AFC comprises methyl furan-2-carboxylate (MFC), and the AFFC comprises methyl 5-formylfuran-2-carboxylate (MFFC).

4 . The process of claim 2 , wherein the physical separation in step c comprises a flash tank.

5 . The process of claim 3 , wherein the physical separation in step d comprises at least two distillation columns.

6 . The process of claim 2 , wherein the first liquid DAFD rich composition comprises from 30 wt. % to 80 wt. % DAFD and alcohol present in an amount of no more than 60 wt. %, each based on the weight of the first liquid DAFD rich composition.

7 . The process of claim 2 , wherein the concentration of DAFD in the first liquid DAFD rich composition is increased by at least 250% over the concentration of DAFD in the crude diester composition.

8 . The process of claim 2 , wherein the vapor AFC composition comprises at least 15 wt. % AFC, and less than 3 wt. % DAFD, each based on the weight of the vapor AFC composition.

9 . The process of claim 2 , wherein the vapor AFC composition comprises AFC and AFFC in a cumulative amount of at least 90 wt. % based on the weight of the vapor AFC composition.

10 . The process of claim 2 , wherein the concentration of AFC in the vapor AFC composition is increased by a factor of at least 15x relative to the concentration of AFC in the second liquid DAFD rich composition.

11 . The process of claim 2 , wherein the purified DAFD vapor composition comprises DAFD in an amount of greater than 99.0 wt. % and less than 1000 ppm ACFC, each based on the weight of purified DAFD vapor composition.

12 . The process of claim 2 , wherein the liquid ACFC composition comprises ACFC in an amount of at least 30 wt. % and DAFD in an amount of less than 50 wt. %.

13 . The process of claim 2 wherein step d comprises separating at least a portion of alcohol from the first liquid DAFD rich composition using a physical separation process to produce:
d(i) a second alcohol composition that is rich in the concentration of alcohol relative to the concentration of alcohol in the first liquid DAFD rich composition; and
d(ii) a second liquid DAFD rich composition comprising DAFD that is rich in the concentration of DAFD relative to the concentration of DAFD in the first liquid DAFD rich composition; and
wherein said process further comprises:
separating at least a portion of AFC from the second liquid DAFD rich composition using a physical separation process to produce:

e(i) a vapor AFC composition that is rich in the concentration of AFC relative to the concentration of AFC in the second liquid DAFD rich composition; and
e(ii) a partially purified liquid DAFD rich composition comprising DAFD and ACFC that is rich in the concentration of DAFD relative to the concentration of DAFD in the second liquid DAFD rich composition; and
separating at least a portion of the DAFD from the partially purified DAFD rich composition using a physical separation process to produce:

f(i) a purified DAFD vapor composition rich in the concentration of DAFD relative to the concentration of DAFD in the partially purified liquid DAFD rich composition; and
f(ii) a liquid ACFC composition that is rich in the concentration of ACFC relative to the concentration of ACFC in the partially purified liquid DAFD rich composition.

14 . The process of claim 12 , wherein the concentration of DAFD in the second liquid DAFD rich composition is at least 85 wt. %, and the concentration of alcohol is less than 0.1 wt. %, each based on the weight of the second liquid DAFD rich composition and the concentration of alcohol.

15 . The process of claim 12 , wherein the concentration of DAFD in the second liquid DAFD rich composition is higher than the concentration of DAFD in the first liquid DAFD rich composition by at least 30 wt %.

16 . The process of claim 12 , wherein the concentration of DAFD in the partially purified liquid DAFD rich composition is at least 95 wt. % and up to 99.9 wt. %, and the amount of ACFC is at least 1.0 wt. %, each based on the weight of the partially purified liquid DAFD rich composition.

17 . The process of claim 12 , wherein the concentration of AFC in the partially purified liquid DAFD rich composition is depleted relative to the concentration of DAFD in the second liquid DAFD rich composition by a factor of at least 750×.

18 . The process of claim 12 , wherein the vapor AFC composition further comprises AFFC, and the concentration of AFC in the vapor AFC composition is at least 15 wt. %, and the concentration of AFFC in the vapor AFC composition is at least 40 wt. %, each based on the weight of the vapor AFC composition.

19 . The process of claim 12 , wherein the concentration of AFC in the vapor AFC composition is higher than the concentrat

Assignees

• Eastman Chem Co

Inventors

• Fontenot Kevin John
• Janka Mesfin Ejerssa
• Parker Kenny Randolph
• Shaikh Ashfaq Shahanawaz

Classifications

• C08G63/785

  characterised by the apparatus used · CPC title

• C08G63/181

  Acids containing aromatic rings · CPC title

• C07D307/68 Primary

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

• C08G63/66

  Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence) · CPC title

• B01D5/003

  within column(s) · CPC title