Method for preparation of 1,4-cyclohexanedimethanol

Patent metadata

Field	Value
Publication number	US-11629112-B2
Application number	US-201917293482-A
Country	US
Kind code	B2
Filing date	Dec 16, 2019
Priority date	Dec 27, 2018
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

The present disclosure relates to a method for preparation of 1,4-cyclohexanedimethanol. According to the present disclosure, two step reduction reactions are conducted using terephthalic acid as starting material, and an isomerization process for increasing the rate of trans isomers of CHDA is introduced therebetween, thereby providing a method capable of stably preparing CHDM with high rate of trans isomers.

First claim

What is claimed is:

1. A method for preparation of 1,4-cyclohexanedimethanol, comprising steps of:
conducting a hydrogenation reaction of terephthalic acid in the presence of a first hydrogenation catalyst to prepare 1,4-cyclohexanedicarboxylic acid (CHDA) comprising cis isomers and trans isomers;
conducting an isomerization reaction of the reaction product of the step 1 in the presence of an isomerization catalyst to isomerizes at least a part of the cis isomers of CHDA into trans isomers; and
conducting a hydrogenation reaction of the reaction product of the step 2 in the presence of a second hydrogenation catalyst to prepare 1,4-cyclohexanedimethanol (CHDM) comprising cis isomers and trans isomers, and
herein the reaction product the step 1 comprises cis isomers and trans isomers of CHDA at a mole ratio of 8:2 to 6:4;
wherein the isomerization catalyst comprises monoclinic system Zirconia, and
wherein the reaction product of the step 2 comprises cis isomers and trans isomers of CHDA at a mole ratio of 4:6 to 2:8.

2. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the weight ratio of the first hydrogenation catalyst and terephthalic acid is 0.01:1 to 3:1.

3. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the first hydrogenation catalyst comprises one or more metals selected from the group consisting of palladium (Pd), rhodium (Rh), ruthenium (Ru), and platinum (Pt).

4. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the first step is conducted at a pressure of 50 to 220 bar, and a temperature of 100 to 300° C.

5. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the weight ratio of the isomerization catalyst to CHDA is 0.1:1 to 5:1.

6. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the step 2 is conducted at a pressure of 20 to 200 bar, and a temperature of 100 to 300° C.

7. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein, by the isomerization reaction of the step 2, among 100 mol % of the cis isomers of CHDA, 50 mol % or more are converted into trans isomers.

8. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the weight ratio of the second hydrogenation catalyst to CHDA is 0.01:1 to 3:1.

9. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the second hydrogenation catalyst comprises one or more metals selected from the group consisting of palladium (Pd), rhodium (Rh), ruthenium (Ru), and platinum (Pt), and one or more metals selected from the group consisting of tin (Sn), iron (Fe), rhenium (Re), and gallium (Ga).

10. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the step 3 is conducted at a pressure of 50 to 220 bar, and a temperature of 100 to 300° C.

11. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the reaction product of the step 3 comprises cis isomers and trans isomers of CHDM at a mole ratio of 4:6 to 2:8.

12. The method for preparation of 1,4-cyclohexanedimethanol according to claim 1 , wherein the first hydrogenation catalyst comprises palladium (Pd), and the second hydrogenation catalyst comprises ruthenium (Ru) and tin (Sn).

Assignees

• Hanwha Solutions Corp

Inventors

• Jang Namjin
• Kim Eun Jeong
• Lee Sun Uk
• Lee Jong Kwon

Classifications

• C07C61/08

  Saturated compounds having a carboxyl group bound to a six-membered ring · CPC title

• C07C51/36

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

• B01J23/44

  Palladium · CPC title

• C07C29/158 Primary

  containing rhodium or compounds thereof · CPC title

• C07C29/147 Primary

  of carboxylic acids or derivatives thereof · CPC title