Sciencemadness Discussion Board

Basic amine question...

jimmyboy - 8-6-2006 at 12:11

ok ethanol plus ammonia gives ethylamine
methanol (or is it formaldehyde?) plus ammonia -> methylamine
what amine does isopropyl alcohol make?
or maybe acetone?

is it as easy as the others -- just mix with ammonia and heat? i couldnt find this anywhere and looked fairly hard.. just looking for simple amine experiments...

[Edited on 9-6-2006 by jimmyboy]

jimmyboy - 8-6-2006 at 19:53

bump..

ordenblitz - 8-6-2006 at 20:30

Ethyl + amine = ethylamine
methyl + amine = methylamine

so maybe .... isopropyl + amine = isopropylamine


first hit on google:
www.chemicalland21.com/industrialchem/organic/ISOPROPYLAMINE...
<quote>
Low molecular amine names are formed by adding '-amine' as a suffix to the name of the parent compound. In substitutive nomenclature, the prefix 'amino-' is placed before the name of the parent compound to denote the functional group in high molecular amines. Synthetic amines are made mostly by reaction of alcohols with ammonia, catalyzed by metals( nickel or copper) or metal oxide at high temperature.

jimmyboy - 8-6-2006 at 22:40

i did glance at that and thought the same thing at first - i also found this that says something totally different in Ullman's -- maybe another route?

"Reductive ammonolysis of acetone yields isopropylamine"

i also have another instance that says you need to have the alkyl halide plus a catalyst with ammonia to form the amine..

so it may not be as simple as just putting isopropanol and ammonia together or is it?



[Edited on 9-6-2006 by jimmyboy]

stoichiometric_steve - 8-6-2006 at 23:32

Quote:
Originally posted by jimmyboy
"Reductive ammonolysis of acetone yields isopropylamine"


oh yeah thats VERY different. can't you people just read a basic o-chem book? i think mr Polv needs to be a bit more rigorous towards the quality of this board.

andresderis - 9-6-2006 at 11:49

wtf have you any degree on chemistry?? omfg

[Edited on 9-6-2006 by andresderis]

DDTea - 9-6-2006 at 16:38

Lab synthesis of amines is done in a few ways...

Reaction of the Alkyl Halide + Ammonia:

CH3-Br + NH3 --> CH3NH2 + NH4Br

But the problem here is that you will get a mixture of mono-, di-, tri-, and even quaternary amines.

The other way is by reduction of Amides, so for example:

CH3COCl (Acetyl chloride) + NH3 --> Acetamide (CH3CONH2)

CH3CONH2 + LiAlH4 --> CH3CH2NH2 (Ethylamine)

Similarly, Nitriles can be reduced to Amines, with the addition of a carbon in the chain:

CH3-CN (Acetonitrile) + LiAlH4 --> CH3CH2NH2 (Ethylamine)

But most people don't have lithium aluminum hydride lying around, and its synthesis can be hairy...so this might not be useful to you.

The third method is with a salt of Phthalimide:

Na(+)Pthalimide(-) + CH3Br , followed by NaOH --> CH3NH2 + Sodium Pthalate

I don't know if this is answering what you're looking for...but oh well.

I also think it's funny that this thread is titled "BASIC Amine.." hahaha, basically...basic..amines..

jimmyboy - 9-6-2006 at 17:47

thanks :) - yes much more helpful - i was reading these things and wanted to see what could be done with easily acquired reagents (within reason) - hmm doesnt seem to be something you could really do at home then - well even if you do end up with a mixture of 1st 2nd and 3rd amines you could still distill and purify.. (just remember to use a hotplate) but the yields would be dismal most likely.. heck ammonia is cheap - so is alcohol and chlorine - maybe not so bad..

[Edited on 10-6-2006 by jimmyboy]

[Edited on 10-6-2006 by jimmyboy]