chloric1
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1089
Registered: 8-10-2003
Location: GroupVII of the periodic table
Member Is Offline
Mood: Stoichiometrically Balanced
|
|
Acetyl Chloride
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? Share your thoughts. When it warms up to zero Celcius outside I might try this little idea.
[Edited on 1/31/2004 by chloric1]
Fellow molecular manipulator
|
|
unionised
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 5109
Registered: 1-11-2003
Location: UK
Member Is Offline
Mood: No Mood
|
|
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
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1089
Registered: 8-10-2003
Location: GroupVII of the periodic table
Member Is Offline
Mood: Stoichiometrically Balanced
|
|
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.
Fellow molecular manipulator
|
|
KABOOOM(pyrojustforfun)
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 254
Registered: 12-10-2002
Location: Iran (pseudoislamic dictatorship of)
Member Is Offline
Mood: exuviating!
|
|
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
Fighter
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 998
Registered: 7-12-2009
Member Is Offline
|
|
What about S2Cl2?
I think this is possible to make Acyl chloride from carboxylic acid by S2Cl2.
Someone tried it?
|
|
Random
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1018
Registered: 7-5-2010
Location: In ur closet
Member Is Offline
Mood: Energetic
|
|
You would need SOCl2 I think.
|
|
Waffles SS
Fighter
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 998
Registered: 7-12-2009
Member Is Offline
|
|
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
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 424
Registered: 8-6-2013
Location: NW SC, USA
Member Is Offline
Mood: Human Sadness - Julian Casablancas & the Voidz
|
|
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.
|
|