Method for preparing 1,3-cyclohexanedicarboxylic acid

Patent metadata

Field	Value
Publication number	US-10717697-B2
Application number	US-201716337910-A
Country	US
Kind code	B2
Filing date	Sep 27, 2017
Priority date	Sep 29, 2016
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

The present invention relates to a method for preparing 1,3-cyclohexanedicarboxylic acid capable of exhibiting excellent activity, of enhancing the reaction efficiency and economic efficiency by using a catalyst having improved durability under the reaction conditions of high temperature and strong acid, of achieving excellent conversion rates by allowing most of reactants to participate in the reaction, and of obtaining products having high purity while minimizing by-products within a shorter period of time. The method for preparing 1,3-cyclohexanedicarboxylic acid may include: reducing isophthalic acid in the presence of a metal catalyst fixed to a silica support and containing a palladium (Pd) compound and a copper (Cu) compound in a weight ratio of 1:0.1 to 0.5.

First claim

The invention claimed is:

1. A method for preparing 1,3-cyclohexanedicarboxylic acid comprising: reducing isophthalic acid in the presence of a metal catalyst fixed to a silica support and containing a palladium (Pd) compound and a copper (Cu) compound in a weight ratio of 1:0.1 to 0.5.

2. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the silica support contained in the metal catalyst has a specific surface area of 100 m 2 /g to 500 m 2 /g.

3. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the total pore volume of the silica support contained in the metal catalyst is be 0.5 cm 3 /g to 2 cm 3 /g.

4. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the average pore diameter of the silica support contained in the metal catalyst is 80 Å to 200 Å.

5. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the metal catalyst includes 0.1% to 10% by weight of the palladium (Pd) compound relative to the silica support.

6. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the step of reducing isophthalic acid includes contacting the isophthalic acid with hydrogen gas.

7. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the step of reducing isophthalic acid is carried out at 50° C. to 350° C.

8. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the step of reducing isophthalic acid is carried out under a pressure of 30 bar to 150 bar.

9. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the metal catalyst is used in an amount of 10 to 80 parts by weight relative to 100 parts by weight of the isophthalic acid.

10. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein the metal catalyst includes a palladium (Pd) compound and a copper (Cu) compound in a weight ratio of 1:0.3 to 0.5.

11. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein a selectivity defined by the following Equation 1 is 90% or more:
Selectivity (%)=[(Amount of 1,3-cyclohexanedicarboxylic acid (mol %)/Amount (mol %) of product)*100].  [Equation 1]

12. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 1 , wherein after a step of reducing isophthalic acid in the presence of a metal catalyst fixed to a silica support and containing a palladium (Pd) compound and a copper (Cu) compound in a weight ratio of 1:0.1 to 0.5, the method further comprises a step of recovering the metal catalyst; and a step of reducing the isophthalic acid in the presence of the recovered metal catalyst.

13. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 12 , wherein the step of recovering the metal catalyst; and the step of reducing the isophthalic acid in the presence of the recovered metal catalyst are repeatedly carried out twice or more.

14. The method for preparing 1,3-cyclohexanedicarboxylic acid of claim 12 , wherein in the step of reducing the isophthalic acid in the presence of the recovered metal catalyst, the conversion rate defined by the following Equation 2 is 45% or more:
Conversion rate (%)=[(Amount of 1,3-cyclohexanedicarboxylic acid added (mol %))−(Amount of 1,3-cyclohexanedicarboxylic acid remaining after reaction (mol %))]/[Amount of 1,3-cyclohexanedicarboxylic acid added (mol %)]*100.  [Equation 2]

Assignees

• Lotte Chemical Corp

Inventors

• Kim Sung Min
• Cha Mi Sun
• Choi Seong Hwan
• Choi Young Heon
• Park Sung Joon
• Yun Chan Yeong
• Seo Young Jong

Classifications

• C07C61/09

  Completely hydrogenated benzenedicarboxylic acids · CPC title

• C07C51/36 Primary

  by hydrogenation of carbon-to-carbon unsaturated bonds · CPC title

• C07C51/50

  Use of additives, e.g. for stabilisation · CPC title

• B01J23/89

  combined with noble metals · CPC title

• B01J21/08

  Silica · CPC title