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Author: Subject: Benzoyl chloride from benzoic acid
ChemichaelRXN
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[*] posted on 8-12-2020 at 15:56
Benzoyl chloride from benzoic acid


What is your experience on this reaction?

With good ventilation, I was wondering what would occur if the benzoic acid was added to this reaction below. Would this be a suitable way to produce and distill off benzoyl chloride?

SnO2 + 4 HCl → (( Cl2 )) + SnCl2 + 2 H2O

(Edited; Sorry this is what would form: SnO2 + 6 HCl → H2SnCl6 + 2 H2O

I was thinking a reaction that forms chlorine like; MnO2 + HCl —> MnCl2 + Cl2 + H2O )




Thanks,

ChemichaelRXN

[Edited on 9-12-2020 by ChemichaelRXN]




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Boffis
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[*] posted on 9-12-2020 at 02:10


? what has tin got to do with benzoyl chloride? Your tin equation is garbage too. Anhydrous stannic oxide is not attached by hydrochloric acid; in fact the reaction goes the other way!!
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ChemichaelRXN
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[*] posted on 9-12-2020 at 08:03


I am a laid back person, so you can just see how you sound...

Germanium, tin and lead oxides
For example, they all react with hydrochloric acid. This can be summarised as: For example, with tin(II) oxide, you get tin(II) chloride and water.


You also apparently get chlorine gas from the tin oxide reaction with hydrochloric acid.

I was thinking of utilizing the chlorine to react with benzoic acid and form benzoyl chloride that you can distill off.

Does anyone know this may work? I encourage creative, innovative thinking.




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clearly_not_atara
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[*] posted on 9-12-2020 at 08:26


Boffis is an excellent chemist, you should listen to him.

Your post contains so many misconceptions it is hard to separate them from each other. In your first post you write SnO2, tin (IV) oxide, but in your second post you mention tin (II) oxide. Neither efficiently produces chlorine by rxn with HCl; you may be thinking instead of MnO2 which gives this rxn. Furthermore chlorine gas cannot convert carboxylic acids to the chlorides. Even if it could, benzoyl chloride cannot be produced in aqueous media due to competing decomposition. Even if it could, the kinetics are highly unfavorable since chlorine would simply escape before it could react. And even they were not, any attempt at distillation would obviously destroy the reactive product BzCl.

In short, this is so far from practical chemistry it might as well be knitting.




[Edited on 04-20-1969 by clearly_not_atara]
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ChemichaelRXN
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[*] posted on 9-12-2020 at 09:06


You can distill benzoyl chloride.

I was talking about SnO2. I must have been misinformed about the chlorine production. That seems how the equation lays out, but like you said it may be MnO2 instead of SnO2 that would produce chlorine. MnO2 + HCl —> MnCl2 + Cl2 + H2O


[Edited on 9-12-2020 by ChemichaelRXN]




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ChemichaelRXN
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[*] posted on 9-12-2020 at 09:21


Here is knitting for you. Those who dare to think outside of the box always seem to get ridiculed.

https://www.prepchem.com/synthesis-of-benzoyl-chloride/

Benzoyl chloride could be prepared by reacting thionyl chloride or phosphorus pentachloride with benzoic acid.

50 grams of dry benzoic acid are treated in a 500 ml flask, with 90 grams of finely pulverized phosphorus pentachloride. The mixture is mixed well, upon which, after a short time, the reaction takes place with an energetic evolution of hydrochloric acid, and the reaction mass becomes liquid. During the reaction a lot of heat is released. After standing a short time, the completely liquid mixture is twice fractionated by collecting fraction which boils at ~ 200° C, yielding 90 % of benzoyl chloride.


[ I was looking for another way. ]

Maybe the chlorine generated from the MnO2 and HCl would be better suited for benzaldehyde for the formation of benzoyl chloride. Benzaldehyde is miscible with water slightly. Anyway, just thought I’d ask.


D40E6602-F164-4D9B-8B7F-1F27FFE40818.png - 43kB




[Edited on 9-12-2020 by ChemichaelRXN]




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Pumukli
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[*] posted on 9-12-2020 at 12:15


I'm not sure I want to "weigh in" really but clearly_not_atara politely reminded you that Boffis is someone here who actually earned good reputation because of his superb work! If he says something regarding a reaction (plan) then it is worth considering to say the least... Now it is starting to feel embarassing but I can tell you the same things about clearly_not_atara too! If he says something regarding chemistry then you can trust it. :-)

I can feel your desire to "think out of the box", I myself like to do this from time to time but there is a difference between "thinking outside the box" and "presenting superficially thought-out ideas".

Regarding your original idea about generating chlorine and using that to prepare benzoyl-chloride from benzoic acid you can be assured that benzoyl-chloride (acid chlorides in general) are soo important reagents that their synthesis is thoroughly studied from lab-to-reactor scale and back! If there was a better route (what was amateur friendly too) then we'd already use it.

Anyways, from benzoic acid to benzoyl chloride you can use the following reagents: PCl5, PCl3, SOCl2, Oxalyl-chloride, TCT. There are probably a handful of other reagents too, in which I'm not 100% sure though. I can think of compounds like S2Cl2 or SCl2, or SiCl4, or SO2Cl2 or a few other inorganic chlorides BUT elemental chlorine is not among them, be it generated from SnO2, MnO2, or any other way. So the basic flaw in your concept is this last tidbit: Cl2 can not be used directly, you must first convert it to another form (PCl5, PCl3, etc) to be usable.
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teodor
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[*] posted on 9-12-2020 at 12:54


Quote: Originally posted by ChemichaelRXN  

(Edited; Sorry this is what would form: SnO2 + 6 HCl → H2SnCl6 + 2 H2O
[Edited on 9-12-2020 by ChemichaelRXN]


This is known not to be happen. As far as I know neither with hydrated form (which forms different compound) no with anhydrous SnO2 which, according to some studies, can go in solution this way only under long reflux with HI. Practically we use a fusion with something to get something water-soluble from this nice compound.
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ChemichaelRXN
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[*] posted on 9-12-2020 at 13:04


Ok, great, thank you for the info., I appreciate it!



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