Sciencemadness Discussion Board

Triethylamine --- for synthesis...

overload - 9-7-2011 at 12:24

3. Discussion

Trimethylamine can be prepared by the action of formaldehyde on ammonium chloride under pressure;1 by the action of formaldehyde and formic acid on ammonia,2 a method which has been checked by one of the editors and is highly recommended; from paraformaldehyde and ammonium chloride;3 and from methyl alcohol, ammonia, and a catalyst.4 The numerous commercial processes which lead to mixtures of methylamines have not been reviewed since they are not convenient for the laboratory.


This preparation is referenced from:

Org. Syn. Coll. Vol. 1, 531
Org. Syn. Coll. Vol. 2, 85
Org. Syn. Coll. Vol. 3, 334
Org. Syn. Coll. Vol. 4, 84

This came from http://www.orgsyn.org/orgsyn/prep.asp?prep=CV1P0528

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I'm interested in the "by the action of formaldehyde and formic acid on ammonia" one. Has anyone had experience with this one? If you have pub access feel free to share the knowledge.

Lambda-Eyde - 9-7-2011 at 13:35

Quote: Originally posted by ScienceSquirrel  
Quote: Originally posted by mr.crow  
So the formaldehyde also acts as a reducing agent and is itself oxidized to formic acid and then to carbon dioxide. I bet a solution of ammonium chloride, acetaldehyde (or paraldehyde) and formic acid would work to form triethylamine. I could be wrong of course. trimethylamine sounds kind of unpleasant


You are wrong.
The reaction of formaldehyde to form amines under these conditions is unique among the aldehydes.