Process for producing imines and/or amines from alcohols

Details Process for producing imines and/or amines from alcohols Process for producing imines and/or amines from alcohols

1990-11-05

1992-04-07

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

564278, 564479, 564480, 564478, C07C25108

Patent

active

051030586

ABSTRACT:
Process for producing aliphatic imines and/or amines from aliphatic monohydric alcohols, such as higher molecular weight oxo alcohols, including ether alcohols, comprising the steps of dehydrogenating the alcohol to an aldehyde in situ in the presence of a zinc oxide and/or zinc salt/metal hydroxide dehydrogenation catalyst and a soluble amount of a primary aliphatic amine which condenses immediately with the aldehyde under reflux conditions, with continuous water removal, to form the corresponding aliphatic imine (Schiff base). The corresponding aliphatic amine can be formed by reducing or reductively aminating the imine in known manner to form corresponding primary, secondary or tertiary amines as desired. The step of forming the imine is most critical, and the present zinc/metal hydroxide dehydrogenation catalyst system has been found to provide a gentle, inexpensive and efficient conversion of the alcohol to the aldehyde for reaction with the gradually-added primary amine, coupled with the continuous removal of the water of condensation in order to prevent undesired secondary reactions which reduce the yield.

REFERENCES:
patent: 2422013 (1947-06-01), Haury et al.
patent: 2513996 (1950-07-01), Haury et al.
patent: 4152353 (1979-05-01), Haberman
patent: 4210605 (1980-07-01), Hoshino et al.
patent: 4788347 (1988-11-01), Sagou et al.

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