Methods for coproduction of terephthalic acid and styrene from ethylene oxide

Patent metadata

Field	Value
Publication number	US-9718755-B2
Application number	US-201615199047-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). In one aspect, processes of the invention coproduce biobased terephthalic acid and biobased styrene.

First claim

What is claimed is:

1. A process for production of a chemical product comprising terephthalic acid or terephthalate by utilizing furan, ethylene oxide, and carbon monoxide as the feedstocks, the process comprising the steps of:
reacting the ethylene oxide and carbon monoxide to form beta propiolactone; and
deriving the chemical product from the beta propiolactone wherein the chemical product comprises at least one of terephthalic acid, a mono or diester of terephthalic aid, and a mono or bis metal salt of terephthalic acid.

2. The process of claim 1 wherein the carbon efficiency of the process is greater than 80%.

3. The process of claim 2 , comprising the step of:
converting the beta propiolactone to an unsaturated compound selected from the group consisting of: acrylic acid, an ester of acrylic acid an acrylate salt and a mixture of any two or more of these and deriving the chemical product from the unsaturated compound.

4. The process of claim 3 , comprising the step of reacting the unsaturated compound with the furan to provide a seven carbon compound containing a cyclohexene ring and deriving the chemical product from the seven carbon compound.

5. The process of claim 4 , further comprising the step of dehydrating the seven carbon compound to provide a compound containing a mono-substituted benzene ring and disproportionating the compound containing the mono-substituted benzene ring to produce at least a portion of the chemical product.

6. The process of claim 5 , wherein the disproportionation of the mono-substituted benzene co-produces benzene.

7. The process of claim 1 , characterized in that two adjacent ring carbon atoms in the benzene ring of the chemical product are derived from the ethylene oxide.

8. The process of claim 1 , wherein at least one of the carbon monoxide; the ethylene oxide and the furan is biobased.

9. The process of claim 1 , wherein, beta propiolactone is reacted with the furan to provide 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid having a structure:

10. A process for production of a chemical product comprising terephthalic acid or terephthalate by utilizing furan, ethylene oxide, and carbonmonoxide as the feedstocks, the process comprising the steps of:
reacting the ethylene oxide and carbon monoxide to form beta propiolactone;
converting the beta propiolactone to an unsaturated compound selected from the group consisting of: acrylic acid, an ester of acrylic acid an acrylate salt;
reacting the unsaturated compound with the furan to provide a seven carbon compound containing a cyclohexene ring;
dehydrating the seven carbon compound to provide a compound containing a mono-substituted benzene ring; and
disproportionating the compound containing the mono-substituted benzene ring to produce the chemical product wherein the chemical product comprises at least one of terephthalic acid, a mono or diester of terephthalic aid, and a mono or bis metal salt of terephthalic acid.

11. The process of claim 10 , wherein the carbon efficiency of the process is greater than 80%.

12. The process of claim 10 , characterized in that two adjacent ring carbon atoms in the benzene ring of the chemical product are derived from the ethylene oxide.

13. The process of claim 10 , wherein at least one of the carbon monoxide; the ethylene oxide and the furan is biobased.

Assignees

• Novomer Inc

Inventors

• Sookraj Sadesh H
• Farmer Jay J

Classifications

• C07C51/14 Primary

  on a carbon-to-carbon unsaturated bond in organic compounds · CPC title

• C07C51/377

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · 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

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title