Claims
- 1. A process for the preparation of ortho-alkylated amines comprising preparing a catalytic intermediate by heating a first aromatic amine with
- (1)aluminum:
- (2)aluminum chloride;
- (3)zinc, having a particle size in the range of from about 20 to 200 mesh, U.S. Standard; and
- (4)optionally, a solvent and subsequently reacting the catalytic intermediate with an alkene and, optionally, a second aromatic amine at elevated temperature and pressure under reaction conditions sufficient to produce the ortho-alkylated aromatic amines.
- 2. The process of claim 1 wherein the first aromatic amine and the second aromatic amine are phenylenediamines.
- 3. The process of claim 2 wherein the phenylenediamines are selected from the group consisting of toluenediamine, diethyltoluenediamine and mixtures thereof.
- 4. The process of claim 1 wherein the first aromatic amine and the second aromatic amine are the same.
- 5. The process of claim 1 wherein the first aromatic amine and the second aromatic are different.
- 6. The process of claim 1 wherein the alkene contains from about two to about six carbon atoms.
- 7. The process of claim 6 wherein the alkene is selected from the group consisting of ethene, propene, butene and mixtures thereof.
- 8. The process of claim 7 wherein the alkene is ethene.
- 9. The process of claim 1 wherein the reaction of the alkene is carried out at a pressure in the range of about 250 to about 1000 psig.
- 10. The process of claim 1 wherein the catalytic intermediate preparation and the reaction of the alkene with the catalyst are carried out in different reactors.
- 11. The process of claim 1 wherein the catalytic intermediate preparation and the reaction of the alkene with the catalyst are carried out in different reactors.
- 12. The process of claim 11 wherein the catalytic intermediate is prepared in a glass lined reactor and the reaction of the alkene with the catalytic intermediate is carried out in a carbon steel reactor.
- 13. A process for the preparation of diethyltoluenediamine comprising preparing a catalytic intermediate by heating a first aromatic amine selected from the group consisting of toluenediamine, diethyltoluenediamine and mixtures thereof with
- (1) aluminum;
- (2) aluminum chloride;
- (3) zinc, having a particle size in the range of from about 20 to 200 mesh, U.S. Standard; and
- (4) optionally, a solvent and subsequently reacting the catalytic intermediate with ethene and toluenediamine.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of application, serial number 419,058 filed Oct. 10, 1989, now abandoned.
US Referenced Citations (12)
Foreign Referenced Citations (5)
Number |
Date |
Country |
560990 |
Jul 1958 |
CAX |
620573 |
May 1961 |
CAX |
1194890 |
Oct 1985 |
CAX |
385794 |
Apr 1973 |
ESX |
823223 |
Nov 1959 |
GBX |
Non-Patent Literature Citations (3)
Entry |
Parshall et al., "Homogeneous Catalysis for Agrochemicals, Flavors and Fragrances," Chemtech, Jun. 1988, pp. 376-383. |
Stroh et al., "Alkylation of Aromatic Amines," Angew. Chem. 69, Jahrg. 1957, No. 4, pp. 124-131. (copy of international edition in English attached). |
Grant et al., Grant & Hackh's Chemical Dictionary, Fifth Edition, p. 118, 1987. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
419058 |
Oct 1989 |
|