Preparation of N-alkyl and N,N-dialkylaniline

Details Preparation of N-alkyl and N,N-dialkylaniline Preparation of N-alkyl and N,N-dialkylaniline

1987-02-12

1989-01-31

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564402, C07C 8506

Patent

active

048017523

ABSTRACT:
The present invention relates to a vapor phase process for the production of N-alkyl and N,N-dialkylaniline by alkylation of aniline with an alcohol, preferably methanol and ethanol, in the presence of a ZSM-5 catalyst. A modified ZSM-5 catalyst has the advantage of high selectivity for N-alkylation while suppressing the formation of undesired by-products, such as toluidines. The molar ratio of silica to alumina in the catalyst is from about 20:1 to 700:1 and preferably from about 30:1 to 200:1. The silica-alumina may be modified with alkali metal, alkali earth metal or transition metal ions, preferably cesium, potassium, magnesium and iron, to form the finished catalyst. The reactants are contacted in the presence of the catalyst at a temperature of from about 300.degree. to 500.degree. C., at a pressure of from about 1 to 3 atmospheres, and at a molar ratio of alcohol to aniline of from about 1 to 6. The feed rates expressed as weight hourly space velocity (g feed/g catalyst/hour) are broadly from about 0.2 to 4.

REFERENCES:
Chen, P. Y. et al. Chemical Abstracts, vol. 107, No. 6705h, (1987).
Chivadze, G. O. et al, Chemical Abstracts, vol 106, No.32432r, (1987).
Chen. P. Y. et al, Stud. Surf. Sci. Catal., vol. 28 pp. 739-746 (1986).
Takamiya et al, "N-Methylation of Aniline with Methanol over Transition Metal Zeolite", Weseda University Report 21 (1975).

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