Sciencemadness Discussion Board

carboxylic acid and thionyl chloride question

smartgene1 - 25-11-2016 at 12:38

when you react thionyl chloride with a carboxylic acid can it react at room temperature or does it got to be heated to produce the desire acid chloride, is the reaction exothermic meaning it produce enough heat by it self to drive the reaction forward

zed - 25-11-2016 at 15:05

Find a relevant procedure, for the acid you are try to convert, and follow that procedure....Exactly.

Keep in mind, if you actually intend to run this reaction, that Thionyl Chloride is more-or-less a war-gas. It, or its breakdown products....... can tear through your lungs like a rampaging Roto-Rooter.

Oh, there I go again, making wild promises.

Now, I have to refresh myself on the specifics, regarding Thionyl Choride.
Just in case I'm wrong.

Yup! It is pretty much, the way I remembered it.

https://en.wikipedia.org/wiki/Thionyl_chloride

While we are on the subject: one of the guys has written up a procedure, for producing Acid Chlorides, from Acids, by treating them with HCl gas, in the presence of acetonitrile.

Oh, Dammit! I did it again. Now, I've gotta go review the procedure.

https://www.youtube.com/watch?v=ExDI9KUW-9Q

OK, if you are acting on an inexpensive substrate. However, on the other hand, if you are trying to produce your Acyl-Chloride with a wildly expensive starting acid.....Phosphorus OxyChloride, might be a better reagent to consider.



[Edited on 25-11-2016 by zed]

[Edited on 25-11-2016 by zed]

[Edited on 25-11-2016 by zed]

CuReUS - 26-11-2016 at 03:52

why not just use good old TCT ? http://chemistry.mdma.ch/hiveboard/novel/000372508.html

[Edited on 26-11-2016 by CuReUS]

smartgene1 - 26-11-2016 at 04:50

I just want to know if the reaction can be preform at room temperature using thionyl chloride and a carboxylic acid to form a acid chloride

zed - 26-11-2016 at 17:50

In that case..... maybe. Look up the conversion of the acid you are interested in, and see how it was done.

Too many acids out there to make a blanket statement. Some might be difficult to convert... requiring some warming. Many, might require cooling to 0-C., to quell the violence of the reaction.

[Edited on 28-11-2016 by zed]