Method for producing N-methyl-p-toluidine for use as an additive for aviation gasoline

Patent metadata

Field	Value
Publication number	US-10875823-B2
Application number	US-201716473289-A
Country	US
Kind code	B2
Filing date	Dec 19, 2017
Priority date	Jan 5, 2017
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

The invention relates to novel methods for preparing N-methyl-p-toluidine for the use thereof as additive for aviation fuel, and to specific catalysts for these methods.

First claim

What is claimed is:

1. A method for preparing N-methyl-p-toluidine, comprising:
reacting p-toluidine with methanol in the presence of at least one catalyst, wherein the at least one catalyst comprises, in the following proportions,
Cu: 45.5-68.0% by weight,
Zn: 12.3-22.5% by weight,
Al: 1.9-4.1% by weight,
and 7.8-28.2% by weight of oxygen, wherein Cu, Zn, Al and oxygen comprise at least 99% by weight, of the total amount of the catalyst.

2. The method according to claim 1 , wherein the catalyst is pretreated by supplying hydrogen at temperatures of at least 150° C.

3. The method according to claim 2 , wherein the pretreatment of the catalyst with hydrogen can take place prior to introduction into the reactor or in the reactor itself.

4. The method according to claim 1 , wherein the catalyst loading is 0.1 to 1.5 kg of p-toluidine per kg of catalyst per hour.

5. The method according to claim 1 , wherein the molar ratio of p-toluidine to methanol is 1:0.7 to 1:5.

6. The method according to claim 1 , wherein the molar ratio of p-toluidine to hydrogen is 1:0.1 to 1:5.

7. The method according to claim 1 , wherein the method is carried out at a temperature of 200 to 300° C.

8. The method according to claim 1 , wherein the at least one catalyst comprises, in the following proportions,
Cu: 47.0-64.1% by weight,
Zn: 14.3-21.5% by weight,
Al: 2.2-3.8% by weight,
and 13.6-25.1% by weight, of oxygen and 0-10% by weight of carbon, wherein Cu, Zn, Al, oxygen and carbon comprise at least 99.5% by weight, of the total amount of the catalyst.

9. The method according to claim 1 , wherein the at least one catalyst comprises, in the following proportions,
Cu: 47.5-60.5% by weight,
Zn: 15.2-19.5% by weight,
Al: 2.5-3.6% by weight,
and 16.2-24.5% by weight, of oxygen and 0-10% by weight of carbon, wherein Cu, Zn, Al, oxygen and carbon comprise at least 99.5% by weight, of the total amount of the catalyst.

10. The method according to claim 1 , wherein the catalyst loading is 0.3 to 1 kg of p-toluidine per kg of catalyst per hour.

11. The method according to claim 1 , wherein the molar ratio of p-toluidine to methanol is 1:1 to 1:3.5.

12. The method according to claim 1 , wherein the molar ratio of p-toluidine to hydrogen is 1:0.5 to 1:4.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Gerdinand Martina
• Dost Rainer
• Krahwinkel Ralf
• Quella Hans-Jurgen
• Ullrich Daniel
• Kurr Patrick

Classifications

• B01J35/45

  Nanoparticles · CPC title

• B01J35/30

  characterised by their physical properties · CPC title

• B01J35/36

  Mechanical strength · CPC title

• C07C209/18 Primary

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• B01J23/72

  Copper · CPC title