Sciencemadness Discussion Board - source of triethylene glycol for making CROWN ETHER?

source of triethylene glycol for making CROWN ETHER?

rockyit98 - 16-9-2019 at 10:01

i need triethylene glycol to make 1,2-bis(2-chloroethoxy)ethane and react them together to make
18-CROWN-6 AKA [1,4,7,10,13,16-Hexaoxacycloöctadecane]
using this procedure.
http://www.orgsyn.org/demo.aspx?prep=CV6P0301

if some one know better route please let me know.

Tellurium - 16-9-2019 at 12:00

I would just buy the TEG, as it is very cheap and readily available. But have you found any informations about the 1,2-bis(2-chloroethoxy)ethane? Synthesis should be easy, but I mean Informations regarding the toxicity? Because "comparable" substances like Bis(chloromethyl)ether are quite toxic and also highly carcinogenic

[Edited on 16-9-2019 by Tellurium]

rockyit98 - 17-9-2019 at 00:13

Quote: Originally posted by Tellurium

I would just buy the TEG, as it is very cheap and readily available. But have you found any informations about the 1,2-bis(2-chloroethoxy)ethane? Synthesis should be easy, but I mean Informations regarding the toxicity? Because "comparable" substances like Bis(chloromethyl)ether are quite toxic and also highly carcinogenic

[Edited on 16-9-2019 by Tellurium]

if they as much as toxic as you say they are perhaps using DEG (Diethylene glycol) to make and bis(chloroethyl) ether and react it with catechol to make Dibenzo-18-crown-6.

[Edited on 17-9-2019 by rockyit98]

Metacelsus - 17-9-2019 at 04:19

Bis(chloroethyl) ether is even worse for toxicity. It's basically mustard gas with O instead of S.

I'd expect 1,2-bis(2-chloroethoxy)ethane to be "not great, not terrible." It's got low vapor pressure so I think normal precautions (gloves, lab coat, fume hood) would be sufficient. I've attached the MSDS from Sigma.

Attachment: msds.pdf (142kB)
This file has been downloaded 295 times

Godrick VanHess - 17-9-2019 at 06:01

Reminds me of sulfur mustard. Not sure how the O will change its chemical properties but I suspect that it will be similar. I'd be sure to take your chemical hygiene seriously here.