lithium and diethylamine

[tantric4hrs]

has anyone once EVER tried to see if lithium will dissolve in anhydrous diethylamine? it would be SO SIMPLE to test and it would change EVERYTHING if it work - even if you need a cosolvent like tertbutanol - isn't this worth a TRY?

[Osmium]

Has DEA suddenly become available OTC for like real cheap or what?

[tantric4hrs]

how cheap is andydrous ammonia? and EDTA IS dirt cheap and every where. besides, EDA is safe and easy to work with, pure NH3 is corrosive, deadly and utterly watched - i'm just saying, wouldn't it be worth a try?

and DEA diethylamine, is not the same as EDA, ethylenediamine - besides the instant panic the initials DEA cause....

and yes, i screwed up in the original post and called it diethylamine - i meant ethylenediamine, sorry

[Osmium]

> how cheap is andydrous ammonia?

Very cheap.

> EDTA IS dirt cheap and every where. besides, EDA is safe and easy to work with,

EDTA is not EDA. And DEA is yet another chemical.

> pure NH3 is corrosive,

Just like the other amines.

> deadly

Not much more deadly than the other amines.

> and utterly watched

Not nearly as watched as DEA.

[lugh]

It doesn't work the way that you think, read these for the reason why  


Synthesis 391-415 (1972)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-kaiser.djvu" target="_blank" title="Download this file">

Organic Reactions 42, 1-47; 320-334 (1992)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-rabideau.djvu" target="_blank" title="Download this file">

J. Am. Chem. Soc. 77, 3230 (1955)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-benkenser1.djvu" target="_blank" title="Download this file">

J. Org. Chem. 48, 2796(1983)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-benkenser2.djvu" target="_blank" title="Download this file">

J. Am. Chem Soc. 74, 5699(1952)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-benkenser3.djvu" target="_blank" title="Download this file">

 

Tetrahedron Letters no. 16, 1-3 (1960)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-benkenser4.djvu" target="_blank" title="Download this file">

  

JCS Perkin I. 475-7 (1975)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-eaborn.djvu" target="_blank" title="Download this file">

Synlett 344-7 (1993)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-eckrich.djvu" target="_blank" title="Download this file">

[tantric4hrs]

anhydrous ammonia is cheap - but very well guarded. and what does DEA have to do with anything? EDTA is ethylenediamine tetracidic acid - can this not be reacted with a base to make EDA? the "metal ammonia solutions" book very clearly states that lithium will dissolve in an diamine. sorry, though, i'm on dial up and it will take me a while to read over those refs.

[tantric4hrs]

Dimethyl Ethylene gycol ether. Na/K - very soluble K - moderate Na, Li, Ca - None Ethyl Methyl Ethylene Glycol ether Na/K - slight Dimethyl Diethylene glycol ether Na/K - very soluble Diethyl Diethylene Glycol ether Na/K - slightly Ethyl Methyl Diethylene Glycol ether Na/K - Moderate Methyl n-propyl Diethylene Glycol ether Na/K - slightly (a) n-Butyl Methyl Diethylene Gycol ether Na/K - very slightly (a) TetraHydroFuran Na/K - slightly 1-Methoxymethyltetrahydrofuran Na/K - Very soluble 1-ethoxymethyltetrahydrofuran Na/K - moderate (b) 2-Methyltetrahydrofuran Na/K - very slightly (a) Dioxan Na/K - None Cyclic tetramer of propylene oxide Na/K - Very soluble 1: 2-Dimethoxypropane Na/K - very slightly (a) Triethylene glycol dimethyl ether Na/K - very soluble Tetraethylene glycol dimethyl ether Na/K - very soluble Ethylenediamine very soluble Na/K - very Methoxyethylamine Na/K - very soluble
(only on proplonged cooling to 193 K)
( slightly at room temp; moderate on cooling to 193 K)
This article goes on to state:

Lithium - doesn't dissolve in dimethylamine but is quite soluble in ethylamine

and BTW, i did read the ENTIRE metal-ammonia solution book

ps - i'm having not luck what so ever trying to read those refs what format are they in? i mean, i can download them, but them my computer has NO idea how to deal with them

[lugh]

If you'd looked at the top of:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/index.html

You would have found this link:

http://www.lizardtech.com/download

[Osmium]

> EDTA is ethylenediamine tetracidic acid - can this not be
> reacted with a base to make EDA?

No. EDTA is NOT the salt of one molecule of ethylenediamine and 4 molecules of acetic acid! You cannot remove the acetic acid part with base, since it isn't a salt.

> and what does DEA have to do with anything?

Well, you mentioned it in the thread title: "lithium and diethylamine"!
Ethylenediamine and diethylamine are two different compounds.

[Rhodium]

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000476990-file_0eum.gif" title="View this image">
EDTA - Ethylenediaminetetraacetic Acid

[tantric4hrs]