Sciencemadness Discussion Board

Acidic alcohols, eg; ethanol with 1M HCl

Cabalaba - 22-6-2016 at 04:56

I used an alcohol, I think methanol with HCl disssolved (the solution was bought from ) to salt out a product after an A-B extraction.
How long before, if ever, most HCl reacts with the alcohol, whether it's methanol, ethanol, etc, and becomes the chloroalkane?
I know with a secondary or tertiary alcohol, it would be a chloroalkane quickly but how long do these supplies keep stock of something like methane with 1.5M HCl?

NEMO-Chemistry - 22-6-2016 at 05:02

Quote: Originally posted by Cabalaba  
I used an alcohol, I think methanol with HCl disssolved (the solution was bought from ) to salt out a product after an A-B extraction.
How long before, if ever, most HCl reacts with the alcohol, whether it's methanol, ethanol, etc, and becomes the chloroalkane?
I know with a secondary or tertiary alcohol, it would be a chloroalkane quickly but how long do these supplies keep stock of something like methane with 1.5M HCl?


Looks like its VERY slow! Sigma sell Methanol in HCl for chromatography apparently, but anyway I found this that suggests its a long process

http://www.eng-tips.com/viewthread.cfm?qid=88469

Looks like a zinc catalyst is needed??

https://sta.uwi.edu/eng/wije/vol0402_jul1973/documents/Methy...

[Edited on 22-6-2016 by NEMO-Chemistry]

diggafromdover - 22-6-2016 at 07:09

Primary alcohols do not react well enough with HCl to offer a reasonable synthesis route.
Secondary alcohols need a catalyst like ZnCl2 or FeCl3 to react with HCl.
Tertiary alcohols react rapidly with HCL.

Yesterday was so warm my tert-butanol melted.

[Edited on 22-6-2016 by diggafromdover]