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Scr0t
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Presumably that would give benzoyl chloride. That could then be reacted and distilled with acetic acid to make acetyl chloride.
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hanjo
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So basically if i follow you reasonement if you have an Carboxylic Acid Anhydride you can virtually make any other Anhydride or Chloride of any
carboxylic acid.
Exemple ( ??) : Acetic anhydride + Sodium butyrate --> Butyryl Cloride + Sodium Acetate
And is this reaction possible Benzoic anhydride + Glacial acetic Acid ---> Anhydride Acetic + Benzoic acid ????
Is this possible ?Someone had any Documents to share about these reactions
Thanks
[Edited on 22-9-2014 by hanjo]
[Edited on 22-9-2014 by hanjo]
[Edited on 22-9-2014 by hanjo]
Hey! Don't put spammy links in your signature. -Polverone
« Dosis facit venenum. » Paracelcsus
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Scr0t
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Quote: Originally posted by hanjo  | So basically if i follow you reasonement if you have an Carboxylic Acid Anhydride you can virtually make any other Anhydride or Chloride of any
carboxylic acid.
Exemple ( ??) : Acetic anhydride + Sodium butyrate --> Butyryl Cloride + Sodium Acetate |
No.
https://www.sciencemadness.org/whisper/viewthread.php?tid=77...
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plante1999
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Best way for benzoyl chloride is to reflux benzotrichloride with benzoic acid, which can be made with toluene and chlorine, benzoic acid can also be
made with toluene. This process is not only cost efficient, but toluene can be extracted from many paint stripper in most country to a cost of about
10$/100 ml of toluene.
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Dr.Bob
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| Quote: Originally posted by hanjo | So basically if i follow you reasonement if you have an Carboxylic Acid Anhydride you can virtually make any other Anhydride or Chloride of any
carboxylic acid.
Exemple ( ??) : Acetic anhydride + Sodium butyrate --> Butyryl Cloride + Sodium Acetate |
No, in most cases you reach an equilibrium, in that some proportion (you can approximate half, for a starting point) will be on each side of the
arrow. At that time, unless there is some driving force, like a way to remove one of the materials from the reaction, say by distillation,
precipitation, volatilazation, or some other means, the reaction will stay a mixture of many things.
But for every reaction there may be a way to shift the equilibrium to one side or the other of the reaction, by using a specific solvent, temperature,
etc to try to remove one material from the reaction. This is why having a product precipitate from the reaction will drive the reaction forward.
But other ways are possible as well. That is why most people use oxalyl or thionyl chloride to make acid chlorides, as both create volatile compounds
when they react with the acid, so the reactions are pretty much one way only. If you start with an excess of one reagent, that can also help push
the reaction towards the other side of the reaction.
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hanjo
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Ok thanks for explanations
Hey! Don't put spammy links in your signature. -Polverone
« Dosis facit venenum. » Paracelcsus
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CuReUS
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magpie ,really amazing write up .
can we make acetyl chloride like this https://www.erowid.org/archive/rhodium/chemistry/anhydrides....
under the title Acetic anhydride from sodium acetate, using S2Cl2
sodium acetate is reacted with S2Cl2 to get that beautiful symmetric molecule which decomposes to give acetic anhydride upon heating.
now instead of heating why cant we chlorinate it or use some strong chlorine donor(aqua regia or hypochlorite,even electrolysis) or chlorine free
radicle(UV)
6 chlorine atoms participate in the reaction totally
1.first the S-S bond breaks to give free radicle S
2.then the C-O bonds on both sides of the S breaks(to try to fulfill S valency),O being more electronegative than S pulls the electron towards itself.
3. finally the Cl simultaneously adds to the S as well as the C
so we get acetyl chloride and thionyl chloride
could someone validate my idea or point out the mistakes
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MARXYZ
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hcl gas generation
Try 85% phosphoric acid and damp rid.
Produces steady stream of gas. No need to worry about suck back. It won't happen.
1/4 inch phosphoric on bottom of Erlenmeyer. Fill to neck with CaCl2. Insert stopper with hose. Voila!
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Chemosynthesis
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| Quote: Originally posted by CuReUS |
under the title Acetic anhydride from sodium acetate, using S2Cl2
sodium acetate is reacted with S2Cl2 to get that beautiful symmetric molecule which decomposes to give acetic anhydride upon heating.
now instead of heating why cant we chlorinate it or use some strong chlorine donor(aqua regia or hypochlorite,even electrolysis) or chlorine free
radicle(UV)
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I am having a very difficult time envisioning where your electrons all go. Could you work out a pictorial mechanism on something like chemsketch next
time? It is free.
I think I misunderstand your reaction. I am actually not sure I am reading the products correctly. Ideally, you could look up bond enthalpies or
dissociation energies and get an idea of what kind of energy you would need input or released for your reaction, and that can give you an idea of the
likelihood of how exergonic or endergonic a reaction is.
Okay, let me answer what I think is your question as best I can as I understand it. First, for the sake of argument, what prevents alpha halogenation
of your chloride, ala the HVZ reaction?
Now, my real answer: no, I find that highly improbable and would expect a Zincke cleavage of the disulfide bond to be far more reasonable than your
proposal, as I understand it.
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Magpie
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Not yet having any use for my homemade acetyl chloride and wanting to do something simple in my lab I decided to do the 3 qualitative tests in
Brewster (1960). I used a large (20mm x 150mm) test tube for all tests. Here's the results:
(1) Hydrolysis. Carefully poured 1mL in 5mls of water. There was some immediate bubbling and the tube got very hot.
CH3-COCl + HOH --> CH3-COOH + HCl
(2) Esterification. Cautiously poured 1 mL in 2 mL of 95% ethanol. Same as above only the reaction was more vigorous. I could only add a
portion at a time. More bubbles and the tube got very hot. Poured into 50mL of water and smelled the ethyl acetate.
CH3-COCl + CH3-CH2-OH --> CH3-C-OOCH2-CH3 + HCl
(4) Reaction with Aniline. Slowly mixed 1mL with 1mL of aniline. This reaction was downright violent. I could only add a drop or two at a
time. Purified the acetanilide and determined its mp to be be 114-115°C.
C6C5-NH2 + CH3-COCl --> C6H5- NH-COCH3 + HCl
The only reason I'm posting these results is to comment on the remarkable reactivity of this compound. It is much greater than that of acetic
anhydride. I know that chloride is a good leaving group, and that one product is a gas (HCl), but does anyone know what else contributes to this
compound's remarkably high reactivity?
[Edited on 27-2-2015 by Magpie]
The single most important condition for a successful synthesis is good mixing - Nicodem
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blogfast25
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With those two 'electron pullers' (O= and -Cl) that C-Cl bond must be highly polarised. I'm not sure, reactivity wise, there's all that much more to
say, really.
Over to the real experts. 
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Magpie
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Blogfast - what you are saying is that the carbon of -COCl is highly electropositive. Therefore it is also highly electrophilic. Is that your point?
Because of the heat generated on hydroysis and esterification I was curious what I would calculate for heats of reaction for the acetyl chloride.
Here's what I found:
(1) hydrolysis: -21.7 kcal/mole
(2) esterification: -18.1 kcal/mole
(3) rx with aniline: -31.09 kcal/mole
These results seem unremarkable.
The single most important condition for a successful synthesis is good mixing - Nicodem
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franklyn
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If someone missed this
http://www.sciencemadness.org/talk/viewthread.php?tid=9&...
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qeezur
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i used to activate acids with better leaving groups back in my benchwork days ... we used SOCl2 ... i know its banned ... but it was the best way if
yield is to be considered ... i can write up my settled methodology if someone is interested ...
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Magpie
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Today I used the remaining 32g of acetyl chloride that I had made almost exactly 1 year ago. It was tainted a dark brown. On cleanup of the glass
bottle I had stored it in (Qorpak Thermoset F217 cap with ptfe liner) I noticed that the cap threads were black with a wipeable corrosion product. So
I am assuming that this is the source of the brown coloration. I do not know what Thermoset 217 is but I would guess it is some kind of phenolic. I
think this is Qorpak's best cap.
The single most important condition for a successful synthesis is good mixing - Nicodem
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clearly_not_atara
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It just has very low barriers to reaction. Acetate is a much weaker leaving group than chloride.
chem.yu.edu.jo/rawash/chem%20611/homeworks/h17.pdf
[Edited on 2-9-2016 by clearly_not_atara]
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The jersey rebel
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acetonitrile, dry HCl and acetic acid can also be used to make acetyl chloride. chem player made a video about it
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