Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: preparation of triethylamine hydrochloride in laboratory
12AX7
Post Harlot
*****




Posts: 4803
Registered: 8-3-2005
Location: oscillating
Member Is Offline

Mood: informative

[*] posted on 3-2-2007 at 10:18


Ethylate some amine (namely, ammonia) then add acid and remove the salt.



Seven Transistor Labs LLC http://seventransistorlabs.com/
Electronic Design, from Concept to Layout.
Need engineering assistance? Drop me a message!
View user's profile Visit user's homepage View All Posts By User This user has MSN Messenger
Levi
Hazard to Others
***




Posts: 196
Registered: 24-1-2007
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 14:20


Sounds like an energetic precursor ;) Does this material have any interesting properties or is it fairly inert?



Chemcrime does not entail death. Chemcrime is death.
View user's profile View All Posts By User
Levi
Hazard to Others
***




Posts: 196
Registered: 24-1-2007
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 14:48


My organic chem knowlege is limited, is this triethlyamine?





Chemcrime does not entail death. Chemcrime is death.
View user's profile View All Posts By User
Chris The Great
National Hazard
****




Posts: 463
Registered: 29-10-2004
Location: Canada
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 15:13


NEt3 is triethylamine, Et being an ethyl group (-CH2-CH3). It's a nice, useful organic base that is not horribly toxic/smelly like pyridine for example.

[Edited on 3-2-2007 by Chris The Great]
View user's profile Visit user's homepage View All Posts By User This user has MSN Messenger
chemrox
International Hazard
*****




Posts: 2921
Registered: 18-1-2007
Location: UTM
Member Is Offline

Mood: psychedelic

[*] posted on 9-2-2007 at 22:55


what is Levi's compound called? With or without the methyl groups.
View user's profile View All Posts By User
Nicodem
Super Moderator
*******




Posts: 4230
Registered: 28-12-2004
Member Is Offline

Mood: No Mood

[*] posted on 10-2-2007 at 01:25


2,4,6-trimethyl-s-triazine with methyls and s-triazine without methyls.

PS: I don't think the original question of the thread was serious. I doub't anybody would ask something so absurd like how to prepare triethylamine hydrochloride.
View user's profile View All Posts By User
LoKi
Harmless
*




Posts: 27
Registered: 27-2-2007
Location: the state of denial
Member Is Offline

Mood: manic

[*] posted on 27-2-2007 at 02:25


Thats funny, I was just pondering how to make triethylamine myself. Wouldn't it be possible with EtI and NH3? Nicoderm, why is such a question absurd?
View user's profile View All Posts By User
not_important
International Hazard
*****




Posts: 3873
Registered: 21-7-2006
Member Is Offline

Mood: No Mood

[*] posted on 27-2-2007 at 05:29


It's a bit silly of a question because it's a pretty simple and basic preparation, appears early on in organic chemistry books at the beginning of the chapter on amines.

You can make it through reacting ammonia with ethyl iodide (or Br or Cl). You won't get really high yields because you get a mix of EtH3NI, Et2H2NI, Et3HNI, and Et4NI; although you can shift which compound is the main product. Add base to free the primary, secondary, and tertiary amines, fractionate them. The primary and secondary amines can be treated with more EtI, the quaternary salt can be converted to the tertiary amine via Hofmann style elimination.

You can also make the ethyl amines by passing a mixture of ammonia and ethanol vapours over heated catalysts.
http://www.patentstorm.us/patents/4683336-description.html
Once again you get a mix, fractionation lets you get the amine(s) you want, unwanted ones with too few or too many alkyl groups can be recycled through the reaction tube to increase yields of the desired amine.

The catalyst can be prepared by dissolving 'nickel' coins in an acid, nitric is best, and pouring the solution of copper and nickel salts into an excess of a solution of sodium or ammonium carbonate or bicarbonate.

Messy routes, but simple - 1st quarter org chem stuff.
View user's profile View All Posts By User
garage chemist
chemical wizard
*****




Posts: 1803
Registered: 16-8-2004
Location: Germany
Member Is Offline

Mood: No Mood

[*] posted on 27-2-2007 at 05:34


Not totally on topic, but related:
Is it possible to remove primary and secondary amines from a tertiary amine by adding an acylating agent (preferably high- boiling, like benzoyl chloride) which should form an amide with the primary and secondary amine but leave the tertiary amine alone? It seems like distillation from benzoyl chloride could be a good method to free triethylamine from those impurities arising from its production (ater fractional distillation, of course).




www.versuchschemie.de
Das aktivste deutsche Chemieforum!
View user's profile View All Posts By User
not_important
International Hazard
*****




Posts: 3873
Registered: 21-7-2006
Member Is Offline

Mood: No Mood

[*] posted on 27-2-2007 at 06:22


That's a not uncommon procedure, except if you use an acyl halide you need to remove the HCl formed with a strong base, else some of the R3N gets trapped as the salt.

For the lighter amines you can also go the route of treating with with the acylating agent, one that is fairly large and hydrophobic in nature, and extract with aqueous acid to remove the free tertiary amine as a salt. (might also add an organic solvent to keep the amides in a liquid form for easier and better extraction).
View user's profile View All Posts By User
Sauron
International Hazard
*****




Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline

Mood: metastable

[*] posted on 27-2-2007 at 07:22


There's an Org/Syn. procedure for making triethylamine hydrochloride free from ethylamine and diethylamine.

Ethylating ammonia will always get you a mixture; also ethylating diethylamine to the tertiary amine is difficult because of steric hindrance and requires forcing conditions.

So, @Levi, it is not a sumd question. There's a whole thread about DEIA which is closely related and I don't think anyone has yet advanced a good prep for that one.

Normally, since TEA free amine is a common H-scavenger, we "make" triethylamine hydrochloride all the time from that. Normally we just throw it away. TEA being cheap (I have maybe 20 L on hand) it doesn't pay to recycle the hydrochloride back to the free amine.
View user's profile View All Posts By User
Nicodem
Super Moderator
*******




Posts: 4230
Registered: 28-12-2004
Member Is Offline

Mood: No Mood

[*] posted on 27-2-2007 at 11:10


Quote:
Originally posted by LoKi
Thats funny, I was just pondering how to make triethylamine myself. Wouldn't it be possible with EtI and NH3? Nicoderm, why is such a question absurd?

I was referring to the absurdness of asking about triethylamine hydrochloride preparation (the question put by the thread originator) and not about the preparation of triethylamine as you infer. Triethylamine hydrochloride is not that very hygroscopic to be much of a problem to prepare, so the question is nearly as silly as if someone would be asking how to prepare NaCl from NaOH. As far as preparing triethylamine you would have to be some kind of a freak to be wanting to prepare it given the cheapness and availability. The reagents required are nearly all more expensive than Et3N itself.
PS: My screen name is not Nicoderm!
View user's profile View All Posts By User
S.C. Wack
bibliomaster
*****




Posts: 2128
Registered: 7-5-2004
Location: Cornworld, Central USA
Member Is Offline

Mood: Enhanced

[*] posted on 27-2-2007 at 14:40


JACS article from Calcutta, er, Kolkata.

Attachment: 35_1781_1913.pdf (211kB)
This file has been downloaded 870 times

View user's profile Visit user's homepage View All Posts By User
Sauron
International Hazard
*****




Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline

Mood: metastable

[*] posted on 27-2-2007 at 19:08


Many many times on this forum I have seen people asking for preps of common, unregulated and simple compounds. Apparently what is easy to buy in one locale may not be easy to buy in another. Or else the fellow wants to make his own for his own reasons. <shrug>

I assume that he does NOT want to know how to acidify TEA under anhydrous conditions, that is trivial. The equivalent of a cook asking how to boil water.

I suppose he wants to build the TEA in an unequivocal fashion and then acidify it, he did say he wants pure triethylamine hydrochloride. Even if he had TEA sitting on the shelf that would mean distilling it before bubbling in dry HCl in an inert solvent.

Anyway I'd cut the guy some slack. At least he didn't ask for a meth recipe.
View user's profile View All Posts By User
LoKi
Harmless
*




Posts: 27
Registered: 27-2-2007
Location: the state of denial
Member Is Offline

Mood: manic

[*] posted on 28-2-2007 at 11:05


Apologies for the misunderstanding, NICODEM. Must have been craving a cigarette at the time.



\"They who can give up essential liberty to purchase a little temporary safety, deserve neither liberty nor safety.\"
-- Benjamin Franklin
View user's profile View All Posts By User

  Go To Top