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madscientist
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OTC diethylamine, the easy way
Earlier, Madog stated that he thought diethylamine could be made from DEET (which he says can be found in non-pressurized 99% form in stores catering
to outdoorsmen), so I took a look at the structure of the molecule. Turns out it's N,N-diethyl-3-methylbenzamide. Upon reacting that with
strongly alkaline aqueous solution and subsequently distilling, diethylamine will be had!
Too easy. 
[Edited on 23-9-2003 by madscientist]
I weep at the sight of flaming acetic anhydride.
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Blind Angel
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One word: Great!
Now for Dimethylamine?.... 
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Madog
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i realised theres a bottle of "maxi deet" in my basement, plastic, 2oz, bottle of 95% DEET, and guess what, the impurities are "other
isomers" 
you can get it at outdoors stores, even if you arn't planning to make diethylamine its good.
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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trinitrotoluene
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In what synthesis is diethylamine useful in?
TNT
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Mumbles
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The first thing that pops into my mind when I hear Diethylamine is LSD(aka Lysergic Acid Diethylamine)
From http://www.osha-slc.gov/dts/sltc/methods/organic/org041/org041.html
"Diethylamine is used:
in preparation of textile finishing agents, surfactants, rubber processing chemicals, agricultural chemicals, and pharmaceuticals.
as a corrosion inhibitor in iron, steel, and metal industries.
as a polymerization inhibitor and catalyst in the polymer industry and as an intermediate in the dye industry.
as a depilatory of animal skins and in electroplating solutions."
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ra_sun423
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diethylamine specifics
to mad scientist:
much appreciated knowledge..
could you be a little bit more specific?
Such as;
- as far as the reaction time time, and the distillation. How long to react, and do you mean reflux?
- as for the distillation... would all the distillate be pure diethylamine? or would it be wise to collect only the fraction that diethylamine boils
at?
thanks for any additional help.. this knowledge will be put to good use.
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madscientist
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Reaction between NaOH and DEET in a solution of water and ethanol (say, 50/50 mixture) should proceed relatively easily at room temperature. I'd
recommend magnetic stirring if possible, and having a heating option available in case the reaction decides to proceed slowly. A sign that the
reaction is proceeding would be heat. I doubt the reaction would take more than an hour or so once started.
Distillation should be simple enough. Diethylamine boils at 56C, ethanol at 78C, water at 100C, and DEET at 111C. Separation of fractions
shouldn't require any special distillation equipment unless your heating mantle unfortunately happens to be a brick of thermite. And yes, I would
recommend collecting only the fraction that comes over at around 56C.
[Edited on 21-10-2003 by madscientist]
I weep at the sight of flaming acetic anhydride.
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ghost711
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little off topic, but...
Method X is VERY secretly distributed..but takes a little (lot) of research to figure out the golden reference (somewhere) in royal society of (...??)
describes a method to biosynthesize the great acid by "tricking" claviceps paspali in to producing it by modifiying the growth substrate to
produce strictly the d- stereoisomer therefore bypassing synthesis or starting materials. Grow it on the "special, modified"
subtrate...extract the goods...chromatograph for the purity freaks...and enjoy. This so called product is called "the natural" and boy oh
boy. Wowee... Dont ya love how nature can synthesize stuff for ya! Amazing. Thats all I can say..Please dont email me regarding the refs/info. As I
have none. Thats not my bag baby! Pays to know certain people I guess. Enjoy the search...takes a year or so to find the specifics. BTW- DEA hates
this shit..amateurs need not apply. Leave this one to the pros. Enjoy!
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madscientist
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That sounds a bit like "I know the future, but I'm not telling you it." How can you know about this, yet not have any useful details
whatsoever to share?
I weep at the sight of flaming acetic anhydride.
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Mumbles
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We spoke of this in American History actually. They didn't come out and say it, but I knew. The Puritans and other colonials did this
accidentally. It extended as far south as the Carribean(sp?). It was theoretically the cause of the Salem witch hunts, besides the economical benefit
of having the village of Salem rejoin the town of salem, but that has nothing to do with the topic. We didn't learn any specifics, but I think it
has something to do with the methods of refridgeration. IE bury, pack with snow, and cover in saw dust. The humidity had something to do with it also,
I believe in the case of the West Indes. The marshes possibly too. Maybe there was something special in the water. Perhaps the "seasoning"
of the waters did something special.
I know this might not be a lot of help, but it may provide a good place to start for any individuals interested. I don't specifically know if the
breed of plant mentioned in the last post is the same, all I know is that the plant in the colonial times was used to make bread and other grain based
goodies.
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ghost711
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yea..that was a bit cryptic I guess
Im not trying to be a cryptic know-it-all here. But- ever wonder why no one talks about making the stuff...and every internet "recipe" out
there is so detailed and outdated that anyone who even attempts it would be taking on a huge investment, requiring elaborate lab equipment, and more
importantly- starting materials that the DeEeAy has long since flagged for decades. If a person is smart- they wouldnt even touch it with a 10-foot
pole. It is distributed online strictly as a novelty. Did the hippies in the 60's and 70's do it this way?- When they came to parties with
gallon jugs of the stuff?? I think not. Using a reference database these days like scifinder scholar turns up hundreds of different juicy tidbits on
circumventing these "perceived" hurdles- one bypassing another to get an end result. People who actually do, do it..are really, truly on a
quest for the correct (current) information for a viable method of clandestine production- not Hoffman's original synth of step by step, tedious
labwork from materials that were handed down to him. And, when they do actually find it--they are not so quick to just give the info away. I did
have one journal reference that I found after a long search of everything that was out there in college libraries, chem journals, alt. knowledge
books, etc. And when I did finally find this- and read it- a big bright light flicked on in me..and a huge grin took over my face. I did not even
want to attempt what was in the text. Having the knowledge was sufficient enough. And that is why the info isn't just "given
out"--its the journey, not the destination. All I can say is- start with claviceps paspali when you begin the search...
GHOST
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madscientist
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I can't imagine any advantages over the well-known ergot process that would make it worth spending so much time searching.
I find the idea of hoarding knowledge to be disgusting. Science, including the clandestine branch, wouldn't have gotten anywhere if it
weren't for people sharing the destination with others, rather than watching them embark on the journey.
http://www.rhodium.ws/chemistry/lsd.synthesis.txt
[Edited on 21-10-2003 by madscientist]
I weep at the sight of flaming acetic anhydride.
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ghost711
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nice
Ok, thats fine i'll bow out of this one. Anyone interested in this is free to explore all the VAST info on this subject at the hive. Just be
very careful will gallons and gallons of claviceps purpurea, phosphorus oxychloride, hydrazine, etc. Im not hiding, or withholding anything- I
mentioned everything I know about the subject already. Case closed.
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Blind Angel
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Would like to know, is there a way to "cut" diethylamine in two yielding Ethylamine and something else? I was thinking of an acidic
environnement con. H<sub>2</sub>SO<sub>4</sub> maybe? (would yield an ethyl sulfate as side product so i'm not sure of
this...)
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Mumbles
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I'm not sure about "cutting" the diethylamine molecule. If you are after Ethylamine, it is often produced in DEA proceedures starting
from Ethanol. It is then reacted further to produce the diethylamine. A few proceedures from the Hive.
Both of those produce produce ethylamine.
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unionised
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I have a nasty feeling that the deet alcohol water diethylamine system would form a nasty set of azeotropes.
You can cleave amines by acid hydrolysis but the reaction is slow. The other product is alcohol.
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acx01b
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sorry my english is not good:
i didnt understand: what is the product free sold contaning the n,n-diethyl amide ?
(what does otc mean? lol)
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blazter
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separation of products
Even if distillation was to fail, I have a feeling one could take advantage of soluabilities of DEET and diethylamine to have a clean separation.
According to the merck index, DEET is insol. in H2O, sol. in alcohol, ether, and benzene. Also, diethylamine HCl is sol. in water, alcohol, and
chloroform and insol. in ether. Not sure exactly about the properties of the freebase, though I would suspect it to similar to methylamine. So its
possible to also use diethylamine's property of forming salts with acids, and somehow partition between organic/water layers.
Hope this helps, someone should try this and see if its feasible.
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If_6_was_9
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| Quote: | Originally posted by ghost711
Method X is VERY secretly distributed..but takes a little (lot) of research to figure out the golden reference (somewhere) in royal society of (...??)
describes a method to biosynthesize the great acid by "tricking" claviceps paspali in to producing it by modifiying the growth substrate to
produce strictly the d- stereoisomer therefore bypassing synthesis or starting materials. Grow it on the "special, modified"
subtrate...extract the goods...chromatograph for the purity freaks...and enjoy. This so called product is called "the natural" and boy oh
boy. Wowee... Dont ya love how nature can synthesize stuff for ya! Amazing. Thats all I can say..Please dont email me regarding the refs/info. As I
have none. Thats not my bag baby! Pays to know certain people I guess. Enjoy the search...takes a year or so to find the specifics. BTW- DEA hates
this shit..amateurs need not apply. Leave this one to the pros. Enjoy!
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I found something about the Proceedings of the Royal Society of London in US patent 3224945. Also see US3219545
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If_6_was_9
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See this too:
https://www.the-hive.ws/forum/showflat.pl?Cat=&Number=44...
(post 446606)
[Edited on 26-5-2004 by If_6_was_9]
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Sandmeyer
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Unsymmetrical secondary aliphatic amines
The route is IMO pretty nice as it avoids the use of reducing agents and chemicals are readily obtainable...
First the benzaldehyde is condensed with an alkylamine, the condensation product is then treated with the alkylhalide of choice and finally hydrolysed
with water/NaOH to give the unsymmetrical amine as a freebase.
Examples:
http://www.orgsyn.org/orgsyn/prep.asp?prep=CV5P0758 (N-methylethylamine, employing alkylhalide)
"This preparation illustrates a general method for the synthesis of N-methylalkylamines. The submitters have used it to prepare
N-methylbutylamine (Note 4) and N-methylallylamine, and the checkers have used it to prepare N-methylisopropylamine (80%), N-methylisobutylamine
(67%), N-methyl-tert-butylamine (52%), and N-methyl-2-methoxyethylamine (55%)."
http://www.orgsyn.org/orgsyn/prep.asp?prep=CV5P0736 (N-methylbutylamine, employing dimethylsulfate)
"The procedure is a general one for the preparation of unsymmetrical aliphatic amines, for the submitters have used it to obtain good yields
of N-methylpentylamine, N-methylhexylamine, N-methylheptylamine, N-ethylbutylamine, N-ethylpentylamine, and N-ethylheptylamine."
They use benzene for the azeotropic removal of water, but toluene of course works too..
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Reverend Necroticus Rex
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An easier route to diethylamine?
I found a possibly far easier way to prepare secondary alkylamines.
Phospham, PN2H, prepared by passing gaseous NH3 over heated phosphorus, yields secondary alkylamines directly from the primary alcohol.
I unfortunately lost the article I had on phosphorus chemistry, that detailed the preperation and use of phosphazines when I formatted my hard drive
recently to purge it of window$ XP, but I distinctly remember it being succesfully used for preparing dialkylamines.
Looks to me, for those who can aqquire or refine phosphorus, to be a practical synthesis for secondary alkylamines.
The sun is shining on a brand new day
Blackened corpses burn where they were slain
Self-flagellation prompts him to confess, Bless me father, for I made this mess.
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garage chemist
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Dimethylformamide, a common solvent used in laboratories, could perhaps be split into dimethylamine and sodium formate by boiling with NaOH.
Would this work?
Also, I think carboxylic acid amides can be split into the acid and the amine group with mineral acid, too. When acetamide is heated with dilute
H2SO4, it soon smells like acetic acid, and the solution contains ammonium ions.
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frogfot
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Have a feeling that DEET is hard to hydrolyse due to shielding of carbonyl group. But anyway, easiest would be to boil the DEET with plain aqueous
NaOH, as mentioned in beginning.. (maby DEET is more soluble in water at high temps..) ..hydrolysis will go faster in plain aqueous soln..
The formed diethylamine could be distilled of, through the whole reaction, with a short fractionating column.
I've never seen this stuff yet.. so I'm not able to test this reaction..
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Phel
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frogfot, you should be able to buy a mosquito repellant at your local pharmacy, containing up to 20% DEET, under the name MyggA. But it is very
expensive.
Norway seems to be free of DEET restrictions, since I've managed to find an insect repellant containing up to 50%.
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