Sciencemadness Discussion Board

Creatine reaction with NaOH

Trifluoroacetic - 27-4-2011 at 17:30

I mixed some creatine with sodium hydroxide solution and heated it to try to make a creatine salt from it but it appears to release a gas that smells like ammonia. Does anyone know what chemical reaction is taking place when it is heated?
What is being formed?

ThatchemistKid - 27-4-2011 at 17:47

http://en.wikipedia.org/wiki/File:Creatine2.png

that iminium in the structure might be a hint to what happened

Trifluoroacetic - 27-4-2011 at 18:34

I was looking at that and figure it must be cleaving at the N by the acetyl side of the molecule.

ThatchemistKid - 27-4-2011 at 19:20

Could be, or possibly hydrolysis of the iminium

Trifluoroacetic - 27-4-2011 at 19:30

I wonder what that would yield and what sodium salt would be produced. I've discovered that adding HCL to the solid mass yields what appears to be ammonium chloride gas.

HydroCarbon - 27-4-2011 at 21:11

Ammonium chloride gas? That doesn't exist. You're probably getting some alkyl amine with small amounts of ammonia coming off as a side reaction.

The sodium salt would likely be of the carboxylic acid.

[Edited on 28-4-2011 by HydroCarbon]

Bot0nist - 28-4-2011 at 06:09

Quote: Originally posted by HydroCarbon  
Ammonium chloride gas? That doesn't exist.
[Edited on 28-4-2011 by HydroCarbon]


http://upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Hyd...

"Hydrochloric acid sample releasing HCl fumes, which are reacting with ammonia fumes to produce a white smoke of ammonium chloride."

Ammonium Chloride 'smoke' can be observed. Not technically a gas, but could easily be mistaken for one.

ThatchemistKid - 28-4-2011 at 13:18

you are probably getting the ketone instead of the iminium.

Trifluoroacetic - 28-4-2011 at 15:14

Quote: Originally posted by HydroCarbon  
Ammonium chloride gas? That doesn't exist. You're probably getting some alkyl amine with small amounts of ammonia coming off as a side reaction.

The sodium salt would likely be of the carboxylic acid.

[Edited on 28-4-2011 by HydroCarbon]
That would make sense because it has an ammonia like smell but it's not quite the same.

Trifluoroacetic - 28-4-2011 at 17:50

Apparently heating creatinine with barium Hydroxide will cause B-methyl hydantoin and ammonia to form. Hydantoins can be further hydrolised in the presence of a base will cause further hydrolysis to occur. I am assuming that sodium hydroxide is doing the same thing to creatine. Is B methyl hydantoin useful for anything?