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Author: Subject: Diethylamine Synthesis
ScienceSquirrel
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[*] posted on 26-8-2008 at 13:17


I have had a quick check on your profile.

I think it is time that you got out there and did some leg work of your own.

If you can come back and tell me why you want to make diethylamine and show that you have looked into methods on your own I will help you further.
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mbrown3391
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[*] posted on 26-8-2008 at 13:20


What did you discern from my profile, exactly?
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not_important
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[*] posted on 26-8-2008 at 18:20


Reaction #3 sounds a bit questionable to be. In the cold NH3 will react with H2SO4 to make ammonium sulfate or bisulfate. If the ethanol is first reacted with H2SO4 to form ethyl sulfate or diethyl sulfate, that will react with ammonia to give ethylamines.

ScienceSquirrel mentioned an OTC method - passing a mixture of NH3 and EtOH vapour over a hot catalyst (a "hot tube" reaction) to form water and mixed ethylamines. The ration of ammonia to ethanol controls which amine is the predominate product, getting the mono- or tri- amines as the major product is easier than doing so for the diamine. The amines can be fractionated and the unwanted amines returned to the feed side to increase yieldds of the wanted amine.

The reactions taking place are generally a complex mess. One series is the dehydrogenation of the alcohol to the aldehyde, which then reacts with ammonia or amine, then reduction by the hydrogen from the alcohol dehydrogenation step. Alkenes and carbenium ions are important in other paths. Various other products are formed in small amounts, so the final product will require fractionation and possible other purification steps.
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Sauron
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[*] posted on 27-8-2008 at 01:27


mrbrown, you are repeatedly asking for spoonfeeding. If you want to know whether or not the ethylamines form azeotropes, LOOK IT UP. One of the main advantages of being on the forum is access to a vast collection of chemical literature you can browse, download, and use. So use it.

Demonstrate some scholarship and if you get stuck, people will help you.

It is to your advantage to avoid appearing to be a cook looking for a recipe to be spoonfed to him, because the forum has no use for such people.




Sic gorgeamus a los subjectatus nunc.
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stoichiometric_steve
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[*] posted on 27-8-2008 at 06:31


mrbrown: what do you want, diethylamine for making acid? if you can't source or make diethylamine, how do you think you can make acid???



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[*] posted on 27-8-2008 at 09:08


MrBrown: Yes, rxn #2 will work with gaseous products as well as gaseous ammonia bubbled through a solution or liquid EtX. The halogenated carbon is easily attacked by the lone electron pair on nitrogen... always. Et2NH is separable by distillation, but you may find this difficult due to the high vapor pressure of all species present. No azeotrope that I can find.

It's great to do your own homework, but sometimes Google can only go so far. If you don't have access to published literature, you may have a difficult time. Erowid, Rhodium etc. can be sketchy sources for chemistry, albeit publicly available. Orgsyn and wikipedia are good resources, but not cookbook for making drugs. If you decide on a chemistry project that you for sure want to undertake, I would recommend visiting a local university to access published literature (you can usually get SciFinder or something similar on their computers). I can think of a few uses for diethylamine besides #25, and don't really care what you use it for. If you're merely curious, power to you.
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[*] posted on 27-8-2008 at 12:35


Thanks to everyone who actually helped me, namely Arrhenius. i will now do some experiments and post my results. I will start with reaction #1 as it seems most promising.
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[*] posted on 27-8-2008 at 15:22
diethylamine


Small quantities of diethylamine an be prepared by basic hydrolysis of OFF (m-diethyltoluamide) followed by careful distillation. OFF is an insect repellent.
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ScienceSquirrel
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[*] posted on 27-8-2008 at 16:24


Quote:
Originally posted by mbrown3391
Thanks to everyone who actually helped me, namely Arrhenius. i will now do some experiments and post my results. I will start with reaction #1 as it seems most promising.


I think I will leave the DEET on the shelf :D
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[*] posted on 27-8-2008 at 19:52


Note that you need water present for the hydrolysis of DEET.

I did some small scale test tube trials hydrolyzing DEET with base and acid. I don't have any good heat sources at home, I am limited to baths of preheated water, which definitely limited my results. I used DEET (100%), water, and various alcohols (mostly EtOH I think) as co-solvents to try and make the mixture single phase. Then I added either aq NaOH, or conc HCl, and heated with water baths.

The desire for water for the hydrolysis reaction and the desire to keep the mix single phase are contradictory. Is ethylene glycol a better co-solvent? My first instinct was to have the bare minimum stoichiometric amount of water present, but I got best results with more, IIRC.

With base, on at least one trial, I got a strong smell of Et2NH, so that was working. I failed to work anything up due to mistakes. I think that, practically, to recover any that way, you would need to distill as you produce it.

With acid, I got nothing. With more heating, maybe it will work. I think the workup would be easier from the acid reaction, but it didn't go for me.

BTW - I don't entirely understand why Et2NH is so suspicious. I know that it is used in making LSD, but compared to the rest of what that synthesis involves, getting/making Et2NH is insignificant. I can't imagine that is the limiting factor for any aspiring LSD maker. I don't know any any other notorious (mis?) uses of it.
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mbrown3391
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[*] posted on 27-8-2008 at 21:20


Good idea, pantone159, I will do reaction at around 55 degrees c in a distillation apparatus as soon as a get a chance to go searching for DEET.

[Edited on 28-8-2008 by mbrown3391]
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[*] posted on 28-8-2008 at 05:52


Quote:
Originally posted by pantone159
I don't know any any other notorious (mis?) uses of it.


Hmmm. N,N-Diethyltryptamine & related indolealkylamines?




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[*] posted on 28-8-2008 at 06:26


The diethyl analogue of PCP?

Reportedly tastes and smells a bit nasty but is stronger than PCP.

[Edited on 28-8-2008 by ScienceSquirrel]
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[*] posted on 28-8-2008 at 06:47


Quote:
Originally posted by pantone159
I did some small scale test tube trials hydrolyzing DEET with base and acid.


Im pretty sure an acid wont work at all. Seems to me that the hydrolysis reaction will produce diethylamine and m-Toluic acid. So a base would be needed to react with the acid product and prevent it from reacting with the deithylamine again. Im not sure what purpose the ethylene glycol plays, however.
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[*] posted on 28-8-2008 at 06:52


Quote:
Originally posted by ScienceSquirrel
The diethyl analogue of PCP?

Reportedly tastes and smells a bit nasty but is stronger than PCP.

[Edited on 28-8-2008 by ScienceSquirrel]


Yes & good thought.

Most garage chemists are unaware of the tremendous range of structural variation in the basic PCP molecule that will wind up producing the same or similar dissociative effects. And diethylamine is likely easier to source that piperidine.

The attached graphic from the Wikin article on PCP shows some of the analog structures of PCP that have known PCP-like effects. Notice that the N,N-diethyl analog appears in the lower right corner.

[Edited on 28-8-2008 by Ritter]

PCP analogs.jpg - 17kB




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[*] posted on 28-8-2008 at 06:59


Amides can be hydrolysed in acidic and basic solution although generally the base catalysed reaction is faster.
Proteins are amides and they are hydrolysed in strong sulphuric acid solution. An excellent example of hydrolysis in sulphuric acid is to be found here :D
http://en.wikipedia.org/wiki/John_George_Haigh
The diethylamine won't react with the toluic acid as the acid formed is only weakly electrophilic and the amine will be protonated making it a very poor nucleophile.
The ethylene glycol cosolvent with water raises the boiling point of the reaction mixture over say water ethanol and keeps the amide in solution.
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[*] posted on 28-8-2008 at 07:00


Maybe someone should make a thread, "Uses of Diethylamine in the Home Drug Lab," so that we can stop littering this one.
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[*] posted on 28-8-2008 at 07:07


Quote:
Originally posted by ScienceSquirrel
The ethylene glycol cosolvent with water raises the boiling point of the reaction mixture over say water ethanol and keeps the amide in solution.


Does it also raise the boiling point of the amide? because if i am planning to do this in a distillation apparatus, i dont really want the amide to stay in solution.
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[*] posted on 28-8-2008 at 07:15


Quote:
Originally posted by mbrown3391
i dont really want the amide to stay in solution.


How do you expect it to react if it's not in solution? This is not solid-phase chemistry. It is solution-phase chemistry.




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[*] posted on 28-8-2008 at 07:17


because it is soluble in water
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ScienceSquirrel
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[*] posted on 28-8-2008 at 07:17


I think you are mixing up the amide with the amine.

If I were you I would reflux the DEET in a solution of potassium hydroxide in ethanol and water and then distill off the ethanol and diethylamine collecting the product in a chilled receiver.
you can then standardise your product against hydrochloric acid and procede with your further chemistry from there.
The amine will be so much more nucleophilic than ethanol or water that it will not interfere with a lot of reactions.
Solutions of dimethylamine in water or water / ethanol are commonly used in the lab as they are easier to handle than the raw amine which is a gas at room temperature.

If you just tell us what you are planning on doing with the stuff you would kill the speculation stone dead.
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[*] posted on 28-8-2008 at 07:17


Quote:
Originally posted by mbrown3391
Maybe someone should make a thread, "Uses of Diethylamine in the Home Drug Lab," so that we can stop littering this one.


Maybe inquiring minds wonder why you are being so paranoid about our curiosity as to what you want to make diethylamine for.




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[*] posted on 28-8-2008 at 07:20


Quote:
Originally posted by mbrown3391
because it is soluble in water


From the DEET MSDS:

Quote:
Solubility in water: practically insoluble in water

Solubility in other solvents: Soluble in ethanol, ether, isopropanol, chloroform, carbon disulfide, alcohol, benzene, propylene glycol, cotonseed oil, ketones, petroleum distillates; sparingly soluble in petroleum ether and glycerin


You need to add an organic co-solvent to your acid or base in order to get it into solution so you can hydrolyze the amide group. Propylene glycol is available OTC on eBay item #220274087412.


[Edited on 28-8-2008 by Ritter]




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[*] posted on 28-8-2008 at 07:26


If you want to make anhydrous diethylamine ( eg free from water or alcohol ) then you are getting into a whole new ballgame.
If I had several kilos of DEET, a properly equipped lab, a few weeks to play with and no other alternative I might attempt it.
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[*] posted on 28-8-2008 at 07:32


Sorry, i was thinking of the amine. so does the ethylene glycol raise the boiling point of the diethylamine?
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