Methods for production of terephthalic acid from ethylene oxide

Patent metadata

Field	Value
Publication number	US-9719037-B2
Application number	US-201615197838-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Jul 1, 2015
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

The present invention provides methods for the production of terephthalic acid and derivatives thereof using ethylene oxide, carbon monoxide and furan as feedstocks. The process is characterized by high yields and high carbon efficiency. The process can utilize 100% biobased feedstocks (EO via ethanol, CO via biomass gasification, and furan via known processes from cellulosic feedstocks).

First claim

What is claimed is:

1. A process for making a chemical product comprising an aromatic diacid or derivative thereof comprising the steps of:
a) treating biomass to produce ethanol;
b) treating biomass to produce carbon monoxide;
c) converting the ethanol to ethylene oxide;
d) contacting ethylene oxide with the carbon monoxide in the presence of a catalyst to form succinic anhydride;
e) oxidizing the succinic anhydride to provide a compound selected from the group consisting of: maleic anhydride, maleic acid, fumaric acid, a mono- or di-ester of fumaric acid, a mono- or di-ester of maleic acid, a mono- or bis-salt of fumaric acid, a mono- or bis-salt of maleic acid, and a mixture of any two or more of these;
f) contacting the compound of step (e) with furan to provide a compound containing a cyclohexene ring;
g) dehydrating the compound containing the cyclohexene ring to provide at least one of an aromatic acid anhydride, an aromatic diacid, a mono- or bis-salt of an aromatic diacid; and a mono- or bis-ester of an aromatic diacid as the chemical product.

2. The process of claim 1 , wherein at least one compound provided by oxidizing the succinic anhydride is maleic anhydride.

3. The process of claim 1 , wherein at least one compound provided by dehydrating the cylcohexene ring is phthalic anhydride.

4. The process of claim 1 , further comprising the step of converting the chemical product of step (g) to at least one of terephthalic acid, a mono- or di-ester of terephthalic aid, a mono- or bis-metal salt of terephthalic acid.

5. The process of claim 1 , wherein the step of oxidizing the succinic anhydride is performed in a continuous flow reactor.

6. The process of claim 5 , wherein the step of oxidizing the succinic anhydride is performed over a solid catalyst.

7. The process of claim 1 , wherein the step of contacting the compound of step (e) with furan is performed in a continuous flow reactor.

8. The process of claim 7 , wherein the step of contacting the compound of step (e) with furan is performed over a solid catalyst.

9. The process of claim 1 , wherein the carbon monoxide is derived from biomass gasification.

10. The process of claim 1 , wherein the furan is derived from a biobased feedstock.

11. The process of claim 1 , characterized in that a carbon efficiency of the process is greater than 80% where carbon efficiency is calculated by: determining the number of carbon atoms contained in a mass of aromatic diacid produced by the process, dividing that number of carbon atoms by the total number of carbon atoms fed to the process in the form of ethanol, carbon monoxide and furan to produce that mass of aromatic diacid.

Assignees

• Novomer Inc

Inventors

• Sookraj Sadesh H

Classifications

• C07D301/03 Primary

  by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds · CPC title

• C10J3/72 Primary

  Other features · CPC title

• C07D493/18

  Bridged systems · CPC title

• C07D307/89

  with two oxygen atoms directly attached in positions 1 and 3 · CPC title

• C07C51/416

  Henkel reaction and related reactions, i.e. rearrangement of carboxylate salt groups linked to six-membered aromatic rings, in the absence or in the presence of CO or CO2, (e.g. preparation of terepholates from benzoates); no additional classification for the subsequent hydrolysis of the salt groups has to be given · CPC title