Method and system embodiments for converting ethanol to para-xylene and ortho-xylene

Patent metadata

Field	Value
Publication number	US-12264116-B2
Application number	US-202318205439-A
Country	US
Kind code	B2
Filing date	Jun 2, 2023
Priority date	Jul 28, 2021
Publication date	Apr 1, 2025
Grant date	Apr 1, 2025

Abstract

Disclosed herein are embodiments of a method and system for converting ethanol to para-xylene. The method also provides a pathway to produce terephthalic acid from biomass-based feedstocks. In some embodiments, the disclosed method produces p-xylene with high selectivity over other aromatics typically produced in the conversion of ethanol to xylenes, such as m-xylene, ethyl benzene, benzene, toluene, and the like. And, in some embodiments, the method facilitates the ability to use ortho/para mixtures of methylbenzyaldehyde for preparing ortho/para xylene product mixtures that are amendable to fractionation to separate the para- and ortho-xylene products thereby providing a pure feedstock of para-xylene that can be used to form terephthalic anhydride and a pure feedstock of ortho-xylene that can be used for other purposes, such as phthalic anhydride.

First claim

We claim:

1. A method, comprising:
providing a stream comprising ethanol by subjecting at least one article to gasification to produce syngas and converting the syngas by gas fermentation to generate the stream comprising ethanol;
contacting the feed stream comprising ethanol with an oxidation catalyst under oxidation conditions to form an oxidation zone effluent stream comprising acetaldehyde;
passing the oxidation zone effluent stream to a dimerization zone and contacting the oxidation zone effluent stream with a dimerization catalyst under dimerization conditions to produce a dimerization zone effluent stream comprising 2-butenal;
passing the dimerization zone effluent stream to a cyclization zone and contacting the dimerization zone effluent stream with a cyclization catalyst under cyclization conditions to form a cyclization zone effluent stream comprising o-methylbenzaldehyde and/or p-methylbenzaldehyde;
passing the cyclization zone effluent stream to a hydrogenation zone and contacting the cyclization zone effluent stream with a hydrogenation catalyst comprising a first Group VIII metal deposited on a support material to produce a hydrogenation zone effluent comprising a non-equilibrium mixture of o-xylene, p-xylene, and m-xylene;
passing at least a portion of the p-xylene from the non-equilibrium mixture to a first reaction zone under first reaction conditions to produce a stream comprising terephthalic acid;
passing the stream comprising terephthalic acid to a second reaction zone under second reaction conditions to produce a stream comprising polyethylene terephthalate;
using the polyethylene terephthalate from the stream comprising polyethylene terephthalate to generate a new article.

2. The method of claim 1 wherein the at least one article and the new article is the same type of article.

3. The method of claim 1 wherein the at least one article is a bottle, and the new article is a new bottle.

4. The method of claim 1 wherein the at least one article is a tire, and the new article is a new tire.

5. The method of claim 4 wherein the at least one article tire is an end of life tire.

6. The method of claim 1 wherein the at least one article is packaging, and the new article is new packaging.

7. The method of claim 1 wherein the at least one article is clothing, and the new article is new clothing.

8. The method of claim 1 wherein the at least one article is a container, and the new article is a new container.

9. The method of claim 1 wherein the at least one article is an industrial component, and the new article is a new industrial component.

10. The method of claim 1 , wherein the hydrogenation catalyst further comprises a second Group VIII metal, a modifier component, or a combination thereof, all deposited on the support material wherein the second Group VIII metal is not the same as the first Group VIII metal.

11. The method of claim 10 , wherein the modifier component is selected from rhenium, tin, an alkali metal, an alkali earth metal, or any combination thereof.

12. The method of claim 10 , wherein the hydrogenation catalyst comprises the modifier component and wherein the support material is carbon, the first Group VIII metal is palladium, and the modifier component is rhenium.

13. The method of claim 1 , wherein the support material is selected from carbon material, a silica, an alumina, a silica-alumina, a titania, a zirconia, a zeolite, a zinc oxide, or any combination thereof.

14. The method of claim 1 , wherein the non-equilibrium mixture of xylenes comprises m-xylene in an amount ranging from 0 wt % to less than 40 wt % of a m-xylene equilibrium concentration.

15. The method of claim 1 , wherein the non-equilibrium mixture of xylenes comprises m-xylene in an amount ranging from 0 wt % to 20 wt % of a m-xylene equilibrium concentration.

16. The method of claim 1 , wherein the non-equilibrium mixture of xylenes comprises m-xylene in an amount ranging from 0 wt % to 5 wt % of a m-xylene equilibrium concentration.

17. The method of claim 1 , wherein the non-equilibrium mixture of xylenes comprises m-xylene in an amount ranging from 0 wt % to 1 wt % of a m-xylene equilibrium concentration.

18. The method of claim 1 , further comprising one or more separation and/or recycling steps, wherein the recycling steps are selected from
(i) recycling at least a portion of the oxidation zone effluent stream to the oxidation zone until a predetermined target concentration of acetaldehyde in the oxidation zone effluent stream is achieved;
(ii) recycling at least a portion of the dimerization zone effluent stream to the dimerization zone until a predetermined target concentration of 2-butenal in the dimerization zone effluent stream is achieved;
(iii) recycling at least a portion of the cyclization zone effluent stream to the cyclization zone until a predetermined target concentration of o-methylbenzaldehyde and/or p-methylbenzaldehyde in the cyclization zone effluent stream is achieved;
(iv) recycling at least a portion of the hydrogenation zone effluent stream to the hydrogenation zone until a predetermined target concentration of xylenes in the hydrogenation zone effluent stream is achieved; and/or
(v) any combination of steps (i), (ii), (iii), and/or (iv).

Assignees

• Battelle Memorial Institute
• Lanzatech Inc
• Lanza Tech Inc

Inventors

• Ramasamy Karthikeyan K
• Guo Mond
• Rosin Richard Russell
• Kocal Joseph Anthony

Classifications

• C07C2521/18

  Carbon · CPC title

• C07C2521/04

  Alumina · CPC title

• C07C2523/44

  Palladium · CPC title

• C07C2523/656

  Manganese, technetium or rhenium · CPC title

• C07C2521/06

  Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof · CPC title