Method for hydrogenating aromatic compounds

Patent metadata

Field	Value
Publication number	US-10329237-B2
Application number	US-201415103652-A
Country	US
Kind code	B2
Filing date	Dec 10, 2014
Priority date	Dec 11, 2013
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

The present invention relates to a method for hydrogenating aromatic compounds with hydrogen in the presence of a catalyst, in which the catalyst comprises ruthenium on a zirconium oxide support material, and also the use of a catalyst comprising ruthenium on a zirconium oxide support material for hydrogenating aromatic compounds.

First claim

The invention claimed is:

1. A method comprising hydrogenating a mixture 2,4- and 2,6-diaminotoluene, in which the 2,4-diaminotoluene is present in a proportion of 70 to 90% by weight, and the 2,6-diaminotoluene is present in a proportion of 10 to 30% by weight, with hydrogen in the presence of a catalyst, wherein: the catalyst comprises ruthenium on a zirconium oxide support material;
the zirconium oxide support material has a BET surface area of 50 to 100 m 2 /g, a pore volume of 0.1 to 0.9 cm 3 /g, and a tapped density of 700 to 1750 kg/m 3 ; and
the catalyst has a BET surface area of 50 to 100 m 2 /g, a pore volume of 0.1 to 0.9 cm 3 /g, and a tapped density of 700 to 1750 kg/m 3 .

2. The method according to claim 1 , wherein the method is carried out continuously.

3. The method according to claim 1 , wherein the method is carried out at a temperature of 50 to 220° C.

4. The method according to claim 1 , wherein the method is carried out at a hydrogen pressure of 100 to 300 bar.

5. The method according to claim 1 , wherein the catalyst comprises ruthenium in an amount of 0.05 to 20% by weight, based on a total weight of the catalyst.

6. The method according to claim 1 , wherein the zirconium oxide support material is present in monoclinic, tetragonal, cubic or amorphous phase or a mixed phase of these modifications.

7. The method according to claim 1 , wherein the zirconium oxide support material is present in monoclinic, tetragonal or a mixed phase of these modifications.

8. The method according to claim 1 , wherein the zirconium oxide support material of the catalyst has a pore size distribution in which more than 50% of the pores present are formed by mesopores having a diameter of 2 nm to 50 nm and the remainder up to 100% by macropores having a diameter>50 nm.

9. The method according to claim 1 , wherein the catalyst has a pore size distribution in which more than 50% of the pores present are formed by mesopores having a diameter of 2 nm to 50 nm and the remainder up to 100% by macropores having a diameter>50 nm.

10. The method according to claim 1 , wherein the zirconium oxide support material of the catalyst has a pore size distribution in which more than 40% of the pores present are formed by macropores having a diameter of >50 nm and the remainder up to 100% by mesopores having a diameter of 2 nm to 50 nm.

11. The method according to claim 1 , wherein the catalyst has a pore size distribution in which more than 40% of the pores present are formed by macropores having a diameter of >50 nm and the remainder up to 100% by mesopores having a diameter of 2 nm to 50 nm.

12. The method according to claim 1 , wherein the hydrogenation is conducted in an organic solvent.

13. The method according to claim 1 , wherein the catalyst is present in a fixed bed.

14. The method according to claim 1 , wherein the catalyst is present in a suspension.

15. The method according to claim 1 , wherein in the mixture of 2,4- and 2,6-diaminotoluene, the 2,4-diaminotoluene is present in a proportion of 75 to 85% by weight, and the 2,6-diaminotoluene is present in a proportion of 15 to 25% by weight.

Assignees

• Basf Se

Inventors

• Schaack Bernd Bastian
• Bock Martin
• Dahmen Kirsten

Classifications

• C07C2101/14

  Chemistry & Metallurgy · mapped topic

• C07C209/72 Primary

  by reduction of six-membered aromatic rings · CPC title

• C07C211/36

  containing at least two amino groups bound to the carbon skeleton · CPC title

• B01J23/462

  Ruthenium · CPC title

• C07C2601/14

  The ring being saturated · CPC title