VSEPR_VOID
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Ethanolamine Synthesis
I searched around and could not find a amateur synthesis of Ethanolamine from ethylene oxide, or anything else. Does anyone have a tips on where to
look.
According to wikipedia, "Monoethanolamine is produced by treating ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and
triethanolamine. The ratio of the products can be controlled by the stoichiometry of the reactants."
I am interested in the mono variety.
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unionised
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There may be a reason for that.
"Ethylene oxide is extremely flammable, and its mixtures with air are explosive. "
" Extinguishing of burning ethylene oxide is complicated by that it can continue burning in an inert atmosphere and in water solutions. "
"Chronic exposure to ethylene oxide is also mutagenic. The International Agency for Research on Cancer classifies ethylene oxide into group 1, meaning
it is a proven carcinogen."
" At concentrations in the air about 200 parts per million, ethylene oxide irritates mucous membranes of the nose and throat; higher contents cause
damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause pulmonary edema and damage the
cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure"
From
https://en.wikipedia.org/wiki/Ethylene_oxide#Fire_and_explos...
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draculic acid69
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In Australia oven cleaner contain s ethanolamine forget which brand but it's clearly labelled on the can.other ppl have reported extracting and
purifying it.
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Fantasma4500
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Dimethylethanolamine is readily available, maybe you could make it from that?
the mono di and tri should have different polarity, ... im thinking maybe you could react the di/triethanolamines with excess ammonia to turn it into
mono, hm?
maybe you'll have to go with fractional distillation, di/triethanolamine appearing to have higher boiling points than mono
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CuReUS
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why don't you make it from glycine ? - https://www.tandfonline.com/doi/abs/10.1080/0039791960808674...
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VSEPR_VOID
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Zinc borohydrid seems like it would be very difficult to buy or make.
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VSEPR_VOID
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Quote: Originally posted by Antiswat | Dimethylethanolamine is readily available, maybe you could make it from that?
the mono di and tri should have different polarity, ... im thinking maybe you could react the di/triethanolamines with excess ammonia to turn it into
mono, hm?
maybe you'll have to go with fractional distillation, di/triethanolamine appearing to have higher boiling points than mono |
I dont not think that would work. De-alkylating the amine, if that is even possible under amatuer conditions, would likely involve exotic conditions.
If anyone knows how this reaction would work I would be interested.
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AvBaeyer
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You can buy the ethanolamine on Amazon - cheap - assuming you are in the US.
https://www.amazon.com/HiMedia-GRM10183-500ML-Ethanolamine-5...
You will spend a lot more screwing around with the pie-in-the sky stuff proposed so far.
AvB
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Elrik
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When I was considering ethanolamine as a dequaternization
reagent I went through my inventory and the place I found it was in my machine shop as a component of water based coolant concentrate. One brand used
triethanolamine as a major component and another brand used an equal mixture of ethanolamine, diethanolamine, and triethanolamine. The latter was
about 15% ethanolamine by volume.
Ethanolamine boils a little high for distillation at standard pressure, but after distilling off the water heptane, xylene, or octane could be added
to form a low boiling azeotrope if needed.
If the synthesis itself is the goal and you just want a small vial of ethanolamine for your collection, perhaps one could react nitromethane with
formaldehyde under suitable conditions and reduce the 2-nitroethanol. That intermediate might also be fun to play with. I've wondered what kind of
catalyst the borate ester or alkoxyboroxine made from 2-nitroethanol or 2-nitropropan-1-ol would be. Assuming such an ester were not a dangerous
explosive
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VSEPR_VOID
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Is nitromethane formed by the reaction beween sodium methyl sulfate and sodium nitrite? Is sodium methyl sulfate prepared the same way as sodium ethyl
sulfate?
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Fantasma4500
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no nitromethane is more difficult than that, iirc chloroacetic acid and NaNO2? others than that andershoveland had a very technical route with
nitroacetone made from acetone and NO2, then oxidizing and reducing that into NM eventually through some equillibrium chemistry glitches
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clearly_not_atara
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Oxirane: wrong! Toxic, lachrymatory, explosive and flammable.
Nitroethanol: wrong! The compound is unstable to heating.
Best way IMO is a Delepine reaction between ethylene chlorohydrin and hexamine, or possibly ethylene bromohydrin if available. There are a couple of
ways to make this, but if you have the right equipment, I think it should be possible to make a stream of ethylene gas by dripping ethanol into hot
(200 C) sulfuric acid and bubble it through some hypochlorite solution.
On a smaller scale, if serine is available, you can just decarboxylate it.
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