Sciencemadness Discussion Board

Acetyl Chloride

chloric1 - 30-1-2004 at 19:24

OK I have made Chromyl Chloride from adding 96% sulfuric acid to a sodium dichromate/sodium chloride mixture about 12 or 13 years ago. My question is if anyone thinks Acetyl chloride can be made from anhydrous Sodium Acetate and Sodium chloride the same way? I wonder if excess chloride might shift equilibrium because the presence of free anhydrous HCL would assist in dehydration? :o Share your thoughts. When it warms up to zero Celcius outside I might try this little idea.

[Edited on 1/31/2004 by chloric1]

unionised - 31-1-2004 at 06:51

What do you think the other product will be?
Anyway, IIRC the traditional way to make acetic anhydride is to react acetyl chloride with sodium acetate.

chloric1 - 31-1-2004 at 09:39

Well the solids left behind would be sodium bisulfate. The volatiles should be acetyl chloride and hydrogen chloride. Also, I figured that extra sulfuric acid would be better. Heres what I think will happen. if the salts are anhydrous then molecules of acetic acid and hydrogen chloride would be produced. With excess sulfuric acid maybe the acetic acid will condense with the hydrgen chloride. But maybe the HCL will evaporate before it reacts:( I shoudl try this soon. ONe simple test for acetyl chloride would be to put a few drops on a cotton wick and ingnite it. It should burn with a green flame and choking HCL vapors.

KABOOOM(pyrojustforfun) - 2-2-2004 at 14:00

acid chlorides are not that easy to make the water on the right side of rxn may hydrolys it (backward rxn). generally (some) chlorides and oxychlorides of S and P are used. but MAYBE you could use chlorosulfonic acid it better gets horny for the water than AcCl does. to do this, you may use the same method u described but with SA replaced with oleum.

Waffles SS - 18-6-2013 at 06:28

What about S2Cl2?
I think this is possible to make Acyl chloride from carboxylic acid by S2Cl2.
Someone tried it?

Random - 18-6-2013 at 15:16

Quote: Originally posted by Waffles SS  
What about S2Cl2?
I think this is possible to make Acyl chloride from carboxylic acid by S2Cl2.
Someone tried it?


You would need SOCl2 I think.

Waffles SS - 18-6-2013 at 20:54

I know PCl3,PCl5,SOCl2,Oxalyl Chloride,TiCl4,Cyanuric Chloride,POCl3 are suitable for converting Carboxylic acid to Acyl chloride but i want to know does S2Cl2 is effective too?Somebody tried it before?
Quote:

The sulphur chlorides also have a range of uses. S2Cl2 can be used to form acid chlorides

R-COOH + S2Cl2 -> R-CO-Cl + 1/2SO2 + 3/2S + HCl

Small-Scale Synthesis of Laboratory Reagents with Reaction Modeling.By Leonid LernerPage190



[Edited on 19-6-2013 by Waffles SS]

subsecret - 20-6-2013 at 20:40

Quote: Originally posted by chloric1  
... sodium bisulfate. The volatiles should be acetyl chloride and hydrogen chloride. Also, I figured...


Acetyl chloride boils at about 52 Celsius. To absorb the excess HCl, could you bubble the vapors (containing acetyl chloride and HCl) through a warm solution of sodium hydroxide? The temperature should be high enough to prevent the acetyl chloride from condensing, while still allowing the HCl to dissolve and react with the chosen base. Just an idea.