Sciencemadness Discussion Board

Triethylamine / Trimethylamine synthesis

plante1999 - 27-4-2011 at 07:52

I have some question , first how can i synthesis Triethylamine / Trimethylamine.
Also i know that Trimethylamine n-oxide is a solid , does the oxide of Triethylamine is a solid or a liquid?

A way that i ave see on wikipedia:

For trymethylamine , with a catalyst.
3 CH3OH + NH3 → (CH3)3N + 3 H2O

Thanks!

[Edited on 27-4-2011 by plante1999]

ScienceSquirrel - 27-4-2011 at 08:11

Best lab preparation for trimethylamine is the Org Syn one;

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1...

mr.crow - 27-4-2011 at 09:02

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

ScienceSquirrel - 27-4-2011 at 09:14

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.

mr.crow - 27-4-2011 at 09:34

Ah, got it!

ItalianChemist - 27-4-2011 at 10:09

I've triethylamine, it's a very volatile and corrosive liquid, it has a ugly odour and is also very flammable and harmful.
I don't know the synthesis but methylamine can be produced by reduction of nitromethane.

plante1999 - 27-4-2011 at 16:30

I have nitromethane , i use it as solvent for plastic.
What catalist should i use if i want to do this:



For trymethylamine , with a catalyst.
3 CH3OH + NH3 → (CH3)3N + 3 H2O

Also for who want to know why want this compound, witch is not avaible for me, i want to atemps this(it is also on the hydrazine thread):

First stage:
carbamine peroxide + trimethylamine(catalyst) → urea + water + trimethylamine n-oxide
(NH2)2CO.H2O2 + (CH3)3N →(NH2)2CO + H2O + (CH3)3NO

second stage:
trimethylamine n-oxide + urea → carbon dioxide + hydrazine + trimethylamine
(CH3)3NO + (NH2)2CO → CO2 + N2H4 + (CH3)3N

overal process:
carbamine peroxide + trimethylamine(catalyst) → carbon dioxide + water + hydrazine + trimethylamine
(NH2)2CO.H2O2 + (CH3)3N → CO2 + H2O + N2H4 + (CH3)3N

[Edited on 28-4-2011 by plante1999]

ItalianChemist - 28-4-2011 at 03:33

Quote: Originally posted by plante1999  
I have nitromethane , i use it as solvent for plastic.
What catalist should i use if i want to do this:



For trymethylamine , with a catalyst.
3 CH3OH + NH3 → (CH3)3N + 3 H2O

[Edited on 28-4-2011 by plante1999]

If you reduce the -NO2 group on nitromethane to -NH2, you obtain methylamine, not trimethylamine.
I haven't got a procedure, but you could try refluxing nitromethane in presence of a source of H2

Melgar - 4-5-2011 at 13:38

Would dimethylethanolamine (DMAE) work? It's available as a nutrition supplement, and you can buy it in bulk from a bunch of different places. Not sure if that OH group would be a problem, or if any old tertiary amine will do.

ScienceSquirrel - 6-5-2011 at 08:35

Quote: Originally posted by plante1999  


Also for who want to know why want this compound, witch is not avaible for me, i want to atemps this(it is also on the hydrazine thread):

First stage:
carbamine peroxide + trimethylamine(catalyst) → urea + water + trimethylamine n-oxide
(NH2)2CO.H2O2 + (CH3)3N →(NH2)2CO + H2O + (CH3)3NO

second stage:
trimethylamine n-oxide + urea → carbon dioxide + hydrazine + trimethylamine
(CH3)3NO + (NH2)2CO → CO2 + N2H4 + (CH3)3N

overal process:
carbamine peroxide + trimethylamine(catalyst) → carbon dioxide + water + hydrazine + trimethylamine
(NH2)2CO.H2O2 + (CH3)3N → CO2 + H2O + N2H4 + (CH3)3N

[Edited on 28-4-2011 by plante1999]


Is that a documented reaction or have you just made it up?
Just because you can write an equation for a reaction does not mean that it will work.
I can write;

N2O + H2O ---> H2O2 + N2

but it is pure unadulterated rocking horse shit!

ItalianChemist - 6-5-2011 at 10:18

Quote: Originally posted by Melgar  
Would dimethylethanolamine (DMAE) work? It's available as a nutrition supplement, and you can buy it in bulk from a bunch of different places. Not sure if that OH group would be a problem, or if any old tertiary amine will do.

Dimethylethanolamine is different from dimethylamine!
Eliminating the -OH can result very difficult

plante1999 - 6-5-2011 at 12:57

Quote: Originally posted by ScienceSquirrel  
Quote: Originally posted by plante1999  


Also for who want to know why want this compound, witch is not avaible for me, i want to atemps this(it is also on the hydrazine thread):

First stage:
carbamine peroxide + trimethylamine(catalyst) → urea + water + trimethylamine n-oxide
(NH2)2CO.H2O2 + (CH3)3N →(NH2)2CO + H2O + (CH3)3NO

second stage:
trimethylamine n-oxide + urea → carbon dioxide + hydrazine + trimethylamine
(CH3)3NO + (NH2)2CO → CO2 + N2H4 + (CH3)3N

overal process:
carbamine peroxide + trimethylamine(catalyst) → carbon dioxide + water + hydrazine + trimethylamine
(NH2)2CO.H2O2 + (CH3)3N → CO2 + H2O + N2H4 + (CH3)3N

[Edited on 28-4-2011 by plante1999]


Is that a documented reaction or have you just made it up?
Just because you can write an equation for a reaction does not mean that it will work.
I can write;

N2O + H2O ---> H2O2 + N2

but it is pure unadulterated rocking horse shit!



myself made equation , but i made it from old document about decarbonylation catalist, and some real reaction that i have see on some of my book.

[Edited on 6-5-2011 by plante1999]

ScienceSquirrel - 6-5-2011 at 13:10

I can see the urea hydrogen peroxide compound reacting with the amine to form the N-oxide but I cannot see it reacting with the urea to form hydrazine.
I do not know a lot about amine oxides but I have never seen a reaction when one does anything like that!