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Author: Subject: Dimethylethanolamine ??????
mario840
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[*] posted on 29-12-2010 at 01:38
Dimethylethanolamine ??????


Hello,

I'm wondering because Picric-A said that reaction 2-chloroethanol with excess dimethylamine for sure gives 2-Dimethylaminoethanol , but i search more "healthy" reaction and i found this (in Survey of industrial chemistry by Philip J. Chenier) :

acetaldehyde + dimethylamine ----------> Dimethylethanolamine ?



1.JPG - 6kB


Is this really can works ??????????????????? Please help, for any help thx v. much. ;)
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TheOrbit
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[*] posted on 29-12-2010 at 02:30


you mean ethylene oxide " not aldehyde"
http://www.patentstorm.us/patents/5663444/description.html
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mario840
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[*] posted on 29-12-2010 at 02:39


yes yes ethylene oxide , thank you
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smuv
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[*] posted on 29-12-2010 at 12:35


Works. Ethylene oxide is very toxic gas. It is also a very potent carcinogen.

Use ethylene chlorohydrin instead. Just as toxic, put not very volatile, so it is easier to store and work with.
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mario840
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[*] posted on 29-12-2010 at 13:32


So just 1 mole 2-chloroethanol and 1 mole dimethylamine and reflux for how long ? you know something more about this reaction ? i will be greatfully
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smuv
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[*] posted on 29-12-2010 at 20:32


No, it would be 2 mol dimethylamine to 1 mol ethylene chlorohydrin.

ClCH2CH2OH + dimethylamine --> ethylene oxide + dimethylammonium chloride
Ethylene oxide + dimethylamine --> dimethylethanolamine

I don't have any experience with this specific case, but I have some with ring opening of aziridines. If I were to do it, I would add the chlorohydrin drop-wise to the commercial 40% aqueous dimethylamine solution cooled on an ice bath. I would use a healthy excess of the dimethylamine (3x or more). After addition allow the stuff to stir for an hour or so. Assuming the Dimethylaminoethanol does not form an azeotrope with water (which it may) purify it via distillation.
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