Al Koholic
Hazard to Self
Posts: 98
Registered: 2-12-2002
Member Is Offline
Mood: Seeking ligand
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Oxirane and Azirane
I've got some nice routes to these two compounds and I just wanted to run everything by you all to see what your thoughts/concerns/advice are/is
to what I am about to propose. I also have a couple of direct questions...
1) Distillation of ethylene glycol from anti-freeze until pure ditstillate is obtained.
2) Reaction of the distillate with conc. HCl (yes I have the JOCS procedure) to chlorohydrin in 12% yeild.
3) Reaction of chlorohydrin with hexamethylenetetraamine in water at 40C to yield a cmpd I cannot name but will further react. If you really want the
name I'll get it tomorrow.
4) This compound is reacted with aqueous ethanolic HCl to yield 2-aminoethanol.
5) 2-aminoethanol + 12N HCl at 60C for some hours to yield the hydrochloride salt.
6) Chlorination of the salt with HCl to yield Cl(CH2)2NH2-HCl. This step replaces the OH with a Cl and there are several routes. Not having access to
thionyl chloride and such, I figure I had to go with the only HCl route I saw. I have a question about this which I will pose momentarily.
7) Reaction of this compound with NaOH(aq) at 50C and 25 torr for 2 hours to yield a colorless oil with bp: 56-58C which will be pure azirane. I have
the synth and will post if needed.
8) Do whatever the hell you want from here with the azirane...
My question about 6) is what kind of conditions do you all think will be good for reacting 2-ethanolamine HCl with HCl to remove the OH group. I know
that other, better cholrinating agents work but I don't have ready access to them (yet). If dry HCl is required what about pydirine as a
solvent? DMSO? Acetone? I don't know. Also, all the steps above have synths that I can obtain at ease but a lot of them are in german (IE:
justus liebigs and chem berichte)....can people translate them? I will just experiment on my own to determine the exact proportions but it might be
nice to know of any hazards...
Now for Oxirane...
Starting with ethylene glycol again (from anti-freeze), we go to chlorohydrin and then straight to oxirane via reaction with Ca(ClO)2. Much more
straight forward. There is also the option to use aqueous NaOH, Mg(OH)2, Ca(OH)2, and others to get it but there is acetaldehyde, and some other
compounds produced in side reactions that I would like to avoid just for purification reasons. With calcium hypochlorite you get oxirane and CO2.
NICE!
Anyway, just to let you all know...no there is no point to any of the end results...just fun along the way!!! Plus these just happen to be very
reactive and there are plenty of more fun pathways to explore with the help of these compounds!!!
Lemme know what you all think of this...
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Ylang-Ylang
Harmless
Posts: 8
Registered: 7-10-2003
Member Is Offline
Mood: No Mood
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If you replaced the OH's of glycol with Cl, perhaps K2O (potash) could be attached, giving oxirane and salt.
Anyone know any REALLY powerful dehydrating agents?
[Edited on 10-10-2003 by Ylang-Ylang]
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KABOOOM(pyrojustforfun)
Hazard to Others
Posts: 254
Registered: 12-10-2002
Location: Iran (pseudoislamic dictatorship of)
Member Is Offline
Mood: exuviating!
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you can simply eliminate steps 1-4. it's all around you. dishwashing liqides, soapes, emulsion paints, polishes, shampoos... just check their
components and choose one that is easier to purify. they usually have 1 or 2 of ethanolamine, di/triethanolamine. I don't understand why step 5
is done @ 60°C. I bet room tempreture and lower temps are ok.
to your question about 6) add your HCl salt + anhydous ZnCl2 to conc aqueous HCl and reflux.
azirane is aziridine isn't it? a tringel with 2 -CH2- and a -NH-
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