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Author: Subject: Ethanolamine Synthesis
VSEPR_VOID
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[*] posted on 18-1-2019 at 17:01
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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[*] posted on 18-1-2019 at 17:20


Quote: Originally posted by VSEPR_VOID  
I searched around and could not find a amateur synthesis of Ethanolamine from ethylene oxide, or anything else.

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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[*] posted on 18-1-2019 at 17:45


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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[*] posted on 19-1-2019 at 02:49


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




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
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[*] posted on 19-1-2019 at 04:09


why don't you make it from glycine ? - https://www.tandfonline.com/doi/abs/10.1080/0039791960808674...
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[*] posted on 19-1-2019 at 08:30


Quote: Originally posted by CuReUS  
why don't you make it from glycine ? - https://www.tandfonline.com/doi/abs/10.1080/0039791960808674...


Zinc borohydrid seems like it would be very difficult to buy or make.




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[*] posted on 19-1-2019 at 08:35


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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[*] posted on 19-1-2019 at 19:23


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.

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[*] posted on 20-1-2019 at 10:43


Quote: Originally posted by draculic acid69  
In Australia oven cleaner contain s ethanolamine
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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[*] posted on 20-1-2019 at 11:50


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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[*] posted on 25-1-2019 at 10:20


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



~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
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[*] posted on 25-1-2019 at 11:28


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.




[Edited on 04-20-1969 by clearly_not_atara]
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