Method for producing toluenediamine

Patent metadata

Field	Value
Publication number	US-10155720-B2
Application number	US-201515310215-A
Country	US
Kind code	B2
Filing date	May 11, 2015
Priority date	May 13, 2014
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

The invention concerns a method for producing toluenediamine by hydrogenation of dinitrotoluene in the presence of a catalyst, a dinitrotoluene being used as starting material and being processed by applying an electrical voltage.

First claim

The invention claimed is:

1. A process for preparing toluenediamine by hydrogenation in the presence of a catalyst of a dinitrotoluene starting material which has been treated by application of an electric potential using a DC voltage of from 50 volt to 1000 volt in a cell having an electrode spacing of from 1 mm to 100 mm for a period of from 0.01 second to 100 seconds.

2. The process of claim 1 , wherein the dinitrotoluene starting material treated by application of an electric potential contains from 90% by mass to 99.5% by mass of dinitrotoluene and from 0.5% by mass to 10% by mass of water.

3. The process of claim 1 , wherein the catalyst is selected from among catalysts containing Pt, Pd, Rh, Ru, Ni, Co, Cu or mixtures thereof and the catalyst is used in a concentration of from 0.01% by mass to <20% by mass, based on the total mass of the reaction mixture in the hydrogenation.

4. A process for preparing toluenediamine, comprising:
(i) dinitrating toluene to form dinitrotoluene;
(ii) working-up the crude process product obtained in step (i) by (ii.1) removal of the aqueous phase and (ii.2) subsequent at least single-stage scrubbing of the dinitrotoluene phase obtained in (ii.1) by means of at least one aqueous scrubbing medium, where each scrubbing stage comprises mixing of the dinitrotoluene phase with aqueous scrubbing medium and subsequent removal of the aqueous scrubbing medium;
(iii) treating the dinitrotoluene by application of an electric potential using a DC voltage of from 50 volt to 1000 volt in a cell having an electrode spacing of from 1 mm to 100mm for a period of from 0.01 second to 100 seconds, where the treatment is carried out before or after removal of aqueous scrubbing medium used in step (ii); and
(iv) hydrogenating the dinitrotoluene starting material treated by application of an electric potential.

5. The process of claim 4 , wherein the scrubbing in step (ii.2) comprises from two to four stages and the aqueous scrubbing medium of at least one of the stages apart from the last stage contains a base.

6. The process of claim 4 , wherein the scrubbing in step (ii.2) comprises from 2 to 6 stages and the aqueous scrubbing medium does not contain a base in any of the stages.

7. The process of claim 4 , wherein the treatment in step (iii) is carried out by application of an electric potential in or after the last scrubbing stage in step (ii.2).

8. The process of claim 7 , wherein the mixing of dinitrotoluene and aqueous scrubbing medium in the last scrubbing stage of step (ii.2) is followed by an electrocoalescence apparatus for treatment of the dinitrotoluene by application of an electric potential in step (iii).

9. The process of claim 7 , wherein an electrocoalescence apparatus for treatment of the dinitrotoluene by application of an electric potential in step (iii) is integrated into the mixing of dinitrotoluene phase and aqueous scrubbing medium in the last scrubbing stage of step (ii.2).

10. The process of claim 7 , wherein the removal of aqueous scrubbing medium in the last scrubbing stage of step (ii.2) is carried out in a phase separation apparatus having a downstream settling tank for taking up the scrubbed dinitrotoluene phase, where the settling tank or a pipe connecting the settling tank to the phase separation apparatus is provided with an electrocoalescence apparatus for the treatment by application of an electric potential in step (iii).

11. The process of claim 10 , wherein water is fed in addition to the scrubbed dinitrotoluene phase into the settling tank and the aqueous phase which settles out is taken off continuously or discontinuously from the settling tank.

12. The process of claim 11 , wherein the aqueous phase is taken off discontinuously.

13. A process for preparing toluenediamine comprising:
(a) treating a dinitrotoluene starting material by application of an electric potential using a DC voltage of from 50 volt to 1000 volt used as electric potential to which the dinitrotoluene starting material is subjected in a cell having an electrode spacing of from 1 mm to 100 mm for a period of from 0.01 second to 100 seconds; and
(b) hydrogenating the treated dinitrotoluene starting material in the presence of a catalyst.

14. The process of claim 13 , wherein the dinitrotoluene starting material treated by application of an electric potential contains from 90% by mass to 99.5% by mass of dinitrotoluene and from 0.5% by mass to 10% by mass of water.

15. The process of claim 13 , wherein the catalyst is selected from among catalysts containing Pt, Pd, Rh, Ru, Ni, Co, Cu or mixtures thereof and the catalyst is used in a concentration of from 0.01% by mass to <20% by mass, based on the total mass of the reaction mixture in the hydrogenation.

Assignees

• Covestro Deutschland Ag

Inventors

• Pennemann Bernd
• Mairata Antoni
• Zock Antonia

Classifications

• C07C201/08 Primary

  by substitution of hydrogen atoms by nitro groups · CPC title

• C07C209/36 Primary

  by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings {in presence of hydrogen-containing gases and a catalyst} · CPC title

• C07C201/16

  Separation; Purification; Stabilisation; Use of additives · CPC title

• B01D2257/80

  Water · CPC title

• B01D17/045

  with coalescers · CPC title