I was going to post this either in the Nitroethane thread, or the Ethyl Bromide thread, but I figured it would be best to make its own thread in an attempt to keep everything on topic, and really this idea, if it works, would allow you to make amines out of ethyl, methyl, and other alcohols.
I was thinking if EtBr reacts with NH3 to form EtNH2, Why wouldn't EtHSO4?
This is my idea that I'll hopefully be able to test sometime soon - even though I've already got to many projects going on right now.
This might be wishful thinking, but it seems to me that Et can act like H in some situations, Ethyl Hydrogen Sulfate is the ethyl analogue of sulfuric acid, and Sodium Ethyl Sulfate is the Ethyl analogue of Sodium Bisulfate with that in mind, I think that a "double salt" of EtNH3 and NH4 can form.
So you'd go about a the reaction something like this..
NaHSO4 + EtOH = Na2SO4*H2O + EtHSO4
NH3 + EtHSO4 = NH4EtSO4
NH3 + NH4EtSO4 = NH4(NH3Et)SO4
NH4NH3EtSO4 =Heat=> NH4HSO4 + EtNH2 (Possibly EtNH2*H2SO4 + NH3, I doubt it though)
Or alternatively if that doesn't work, when other acids are added to sulfates, Bisulfates form which might allow you to do something like this..
NH4(NH3Et)SO4 + HCl = NH4HSO4 + EtNH2*HCl
The mixture could then be neutralized with NH3 to form free EtNH2.
I don't see why this wouldn't work, and if it is impossible to do I apologize for the post - I haven't' looked up much information on this since the compound NH4NH3EtSO4 is difficult to find on the internet.. perhaps poor searching skills or it just doesn't exist since it may rearrange into (EtNH2)2*H2SO4 and (NH4)2SO4
Either way do you guys have any input on this? I think this could be a useful route to methylamine, ethylamine, isopropylamine and various other alkylamines from their corresponding alcohols if it works.
Dimethyl sulfate can form methylamine with reaction of ammonia according to: Ephrian and Gurewitsch, Ber. 43, 139 (1910); Denham and Knapp, J. Chem. Soc. 117, 236 (1920). (source taken from http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0347#Ref349N6)
I figure Methyl Hydrogen Sulfate would do the same.
I was thinking if EtBr reacts with NH3 to form EtNH2, Why wouldn't EtHSO4?
This is my idea that I'll hopefully be able to test sometime soon - even though I've already got to many projects going on right now.
This might be wishful thinking, but it seems to me that Et can act like H in some situations, Ethyl Hydrogen Sulfate is the ethyl analogue of sulfuric acid, and Sodium Ethyl Sulfate is the Ethyl analogue of Sodium Bisulfate with that in mind, I think that a "double salt" of EtNH3 and NH4 can form.
So you'd go about a the reaction something like this..
NaHSO4 + EtOH = Na2SO4*H2O + EtHSO4
NH3 + EtHSO4 = NH4EtSO4
NH3 + NH4EtSO4 = NH4(NH3Et)SO4
NH4NH3EtSO4 =Heat=> NH4HSO4 + EtNH2 (Possibly EtNH2*H2SO4 + NH3, I doubt it though)
Or alternatively if that doesn't work, when other acids are added to sulfates, Bisulfates form which might allow you to do something like this..
NH4(NH3Et)SO4 + HCl = NH4HSO4 + EtNH2*HCl
The mixture could then be neutralized with NH3 to form free EtNH2.
I don't see why this wouldn't work, and if it is impossible to do I apologize for the post - I haven't' looked up much information on this since the compound NH4NH3EtSO4 is difficult to find on the internet.. perhaps poor searching skills or it just doesn't exist since it may rearrange into (EtNH2)2*H2SO4 and (NH4)2SO4
Either way do you guys have any input on this? I think this could be a useful route to methylamine, ethylamine, isopropylamine and various other alkylamines from their corresponding alcohols if it works.
Dimethyl sulfate can form methylamine with reaction of ammonia according to: Ephrian and Gurewitsch, Ber. 43, 139 (1910); Denham and Knapp, J. Chem. Soc. 117, 236 (1920). (source taken from http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0347#Ref349N6)
I figure Methyl Hydrogen Sulfate would do the same.
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