Sciencemadness Discussion Board

Diethanolamine from 2-Chloroethanol

JessePAA - 9-6-2019 at 09:04

I know that preparation of 2-Chloroethanol is done easily by this reaction:

C2H6O2 + HCl = HOCH2CH2Cl + H2O

(ethylene glycol + hydrogen chloride at 100°C = 2-Chloroethanol + water)

I only have 1 reference from a guy that says reacting 2-Chloroethanol with ammonia will give a mixture of monoethanolamine, diethanolamine and triethanolamine and that can be distilled, but he didn't specify quantities or if any heat is needed etc.

I tried searching for hours but I'm stuck and I wanted to know if anyone here could please point me into the right direction of finding the correct quantities and figure out what the chemical equation is for this reaction?

Thank you.

Pumukli - 9-6-2019 at 09:37

"and figure out what the chemical equation is for this reaction?"

Isn't this reaction a bit too ambitious for you? I mean, you in your first post (wellcome, by the way!) states that making chloroethanol is easy - but trust me, with time you will learn that nothing is so easy or straightforward in organic chemistry! :)

Then you have problems figuring out the equation(s) for ammonia and chloroethanol. It is not that complicated!
Read (general org. chem books are fine), learn, and you will be able to figure out those equations soon! You can learn a lot of things if you read the latest few hundred topics in this forum too! (Read lots of preparation recipes, synth descriptions and you will realise that nothing is that easy, but I already told you this.)

But please, before you attempt such "easy" syntheses please learn the basics at least!

What is your educational background? Your equipments? Can you perform an "easy" vacuum distillation with your gear? Diethanolamine boils around 270 C, you probably don't want to distill it at normal pressure!

Several people here could give you those equations but then your learning experience would suffer.

Don't let my ramblings ruin your mood but I felt that you found a bit too hard "easy" reaction for yourself! :)

JessePAA - 9-6-2019 at 10:36

It is very ambitious, I don't know very much chemistry and this reaction so far is all theory, I don't even have the glassware to do the synthesis.

I don't have a chemistry background / knowledge apart from watching NileRed and Nurdrage on YouTube, I know that there are many things I'm not taking into consideration like what type of glassware, the temperatures, the toxicity of 2-Chloroethanol, personal protection etc.


I do read some books on chemistry but generally i learn better if i see it actually done, I could figure this out if i really took my time but as i said I'm kinda lost and want a little help.

I just wanna state again, I won't do this synthesis (yet), I just want to know the theory behind it so if I ever try it I don't waste tons of chemicals figuring it out. (not that ethylene glycol is very expensive).

JessePAA - 9-6-2019 at 12:37

Actually, might it be this?

2 C2H6O2 + NH3 = C4H11NO2 + 2 H2O

Of course Diethanolamine is not the only thing formed but also Monoethanolamine and Triethanolamine, right?'


EDIT: nevermind, I finally figured it out.

https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE...

This is the russian wikipedia page for ethanolamine, it directly says this:
Quote:

In industry, ethanolamine synthesis is carried out by adding ammonia to ethylene oxide in the presence of a small amount of water. The process is carried out in one stage at a temperature of 90-130 ° C and a pressure of 7-10 MPa.

Along with monoethanolamine, diethanolamine and triethanolamine are obtained. When the ratio of ethylene oxide / ammonia (1:15) in the reaction products contains 78.3% mono-, 16% di- and 4.4% triethanolamines. Ethylene oxide in the reaction reacts completely.

The ratio of ethanolamines in the mixture is controlled by the concentration of NH3, the process temperature and the re-direction of the reaction of one or two ethanolamines.

The resulting mixture of ethanolamines, H2O and NH3 is separated by distillation, and the ammonia in the liquefied form is re-sent to the reactor.

In the laboratory, ethanolamine is obtained by the action of ammonia on ethylene chlorohydrin (2-chloroethanol):

HOCH2CH2Cl + NH3 = HOCH2CH2NH2 + HCl


So, the equation is HOCH2CH2Cl + NH3 = HOCH2CH2NH2 + HCl, the tempurature is 90-130 ° C and the pressure is.... 70 to 100 bar? Isn't that an error? Or is that just for ethylene oxide and not for 2-chloroethanol?

[Edited on 9-6-2019 by JessePAA]

[Edited on 9-6-2019 by JessePAA]

draculic acid69 - 11-6-2019 at 00:26

Start here 2chloro ethanol synthesis video
https://m.youtube.com/watch?v=bKiXxoRZ_VQ

JessePAA - 11-6-2019 at 08:18

Quote: Originally posted by draculic acid69  
Start here 2chloro ethanol synthesis video
https://m.youtube.com/watch?v=bKiXxoRZ_VQ


Very useful video, thank you, I will save it for the future just in case.

Do you have any idea about the required pressure of 2-Chloroethanol to Diethanolamine is really that high or if that just applies to ethylene oxide?

Again thank you.

draculic acid69 - 15-6-2019 at 07:26

Don't know about that, just the 2cloroethanol

draculic acid69 - 15-6-2019 at 07:29

I wonder if that same rxn that turns ethylene glycol into 2cl,etoh works on 1,3 propyl and neopentyl glycols

Chemi Pharma - 15-6-2019 at 07:33

Quote: Originally posted by JessePAA  
Quote: Originally posted by draculic acid69  
Start here 2chloro ethanol synthesis video
https://m.youtube.com/watch?v=bKiXxoRZ_VQ


Very useful video, thank you, I will save it for the future just in case.

Do you have any idea about the required pressure of 2-Chloroethanol to Diethanolamine is really that high or if that just applies to ethylene oxide?

Again thank you.


@Draculic acid gave you the way to 2 chloro ethanol. From this to ethanol-amine you can do a Delepine reaction with HMTA, amination with ammonia and CUSO4 or Gabriel Synthesis with Phtalimide sodium or potassium salt, like said in this papers I attached:



Attachment: Phthalimide - Gabriel amines synthesis - alkyl phtalimide.pdf (396kB)
This file has been downloaded 663 times

Attachment: amination with Hexamethylenetetramine-Delepine Reaction.pdf (14kB)
This file has been downloaded 436 times

Attachment: amination of halides with ammonea and CUSO4.doc (90kB)
This file has been downloaded 438 times