Method for preparing terephthalic acid, and terephthalic acid prepared therefrom

Patent metadata

Field	Value
Publication number	US-12441675-B2
Application number	US-202318726819-A
Country	US
Kind code	B2
Filing date	Aug 30, 2023
Priority date	Sep 5, 2022
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

The present invention relates to a method for preparing terephthalic acid, and terephthalic acid prepared therefrom. Specifically, according to one embodiment of the present invention, by including the step of hydrolyzing a compound prepared by depolymerizing a waste polyester using a specific hydrolysis catalyst, terephthalic acid can be prepared in an environmentally friendly manner, and high purity terephthalic acid can be provided.

First claim

The invention claimed is:

1. A process for preparing terephthalic acid, which comprises:
hydrolyzing bis (2-hydroxyethyl) terephthalate (BHET) or a compound which is liquid at room temperature and is prepared by depolymerizing waste polyester,
wherein the depolymerizing comprises alcoholysis, and the alcoholysis is carried out using an alcohol having 4 or more carbon atoms, and
wherein a hydrolysis catalyst is used in the hydrolyzing and comprises at least one selected from the group consisting of NaOH, NaHCO3, Na 2 CO 3, NaOMe, KOH, K 2 CO 3, KOtBu, CsOH, Ca(OH) 2, LiOH, NH 4 OH, Na 2 TPA, and sodium monobutyl terephthalate.

2. The process for preparing terephthalic acid of claim 1 , wherein the amount of the hydrolysis catalyst used is 0.01 mole to 1.0 mole based on 1 mole of the compound.

3. The process for preparing terephthalic acid of claim 1 , wherein the hydrolysis is carried out at a temperature of 180° C. to 280° C. for 0.5 hour to 24 hours.

4. The process for preparing terephthalic acid of claim 1 , wherein water is added in the hydrolysis step, and the water is added in an amount of 1 to 500 times the weight of the compound.

5. The process for preparing terephthalic acid of claim 1 , wherein the compound is represented by Formula 1:

in Formula 1, R 1 is a substituted or unsubstituted alkyl group.

6. The process for preparing terephthalic acid of claim 5 , wherein R 1 is an alkyl group unsubstituted or substituted with a hydroxy group, or a substituted or unsubstituted alkyl group having 2 or more carbon atoms.

7. The process for preparing terephthalic acid of claim 5 , wherein the compound is dibutyl terephthalate (DBTP), or diisooctyl terephthalate (DOTP).

8. The process for preparing terephthalic acid of claim 1 , wherein an alcohol is produced as a by-product in the hydrolysis step, and the decomposition rate of the alcohol is less than 10%.

9. The process for preparing terephthalic acid of claim 1 , wherein the weight ratio of the waste polyester to the alcohol in the alcoholysis is 1:1 to 10, and the alcoholysis is carried out at a temperature of 160° C. to 280° C. and a pressure of 1 bar to 40 bar for 0.5 hour to 24 hours.

10. The process for preparing terephthalic acid of claim 1 , wherein the process further comprises purifying the compound before the hydrolysis step.

11. The process for preparing terephthalic acid of claim 10 , wherein the purification step comprises adding at least one adsorbent selected from the group consisting of activated carbon, silica gel, alumina, zeolite, and activated clay, or adsorption through bed adsorption, and the content of the adsorbent added is 0.1% by weight to 20% by weight based on the total weight of the compound.

12. Recycled terephthalic acid, which is prepared according to a process for preparing terephthalic acid, which comprises:
hydrolyzing a compound which is liquid at room temperature and is prepared by depolymerizing waste polyester,
wherein the depolymerizing comprises alcoholysis, and the alcoholysis is carried out using an alcohol having 4 or more carbon atoms, and
wherein a hydrolysis catalyst is used in the hydrolyzing and comprises at least one selected from the group consisting of NaOH, NaHCO 3, Na 2 CO 3, NaOMe, KOH, K 2 CO 3, KOtBu, CsOH, Ca (OH) 2, LiOH, NH 4 OH, Na 2 TPA and sodium monobutyl terephthalate, and
wherein the recycled terephthalic acid has a total metal content of less than 100 ppm when measured by inductively coupled plasma atomic emission spectroscopy (ICP-AES).

13. The recycled terephthalic acid of claim 12 , wherein the recycled terephthalic acid has a total content of Sb, Ti, and Zn of less than 30 ppm when measured by inductively coupled plasma atomic emission spectroscopy (ICP-AES).

14. The recycled terephthalic acid of claim 12 , wherein the recycled terephthalic acid has a color-b of less than 2 as measured with a colorimeter, and
the yellow index (Y.I.) is less than 2 when the recycled terephthalic acid is diluted to a concentration of 5% in dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), or methylpyrrolidone (NMP), respectively, and measured.

15. A polyester resin, which comprises the recycled terephthalic acid of claim 12 .

Assignees

• Sk Chemicals Co Ltd

Inventors

• Chang Yu-Mi
• Kang Ju-Sik
• Park Jeong Ho
• Chae Hee-Il

Classifications

• C08G63/183

  Terephthalic acids · CPC title

• C07C63/26

  1,4 - Benzenedicarboxylic acid · CPC title

• C07C67/56

  by solid-liquid treatment; by chemisorption · CPC title

• C07C67/03

  by reacting an ester group with a hydroxy group · CPC title

• C08J11/14

  by treatment with steam or water · CPC title