Johnny Windchimes
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The Synthesis of Benzoyl Chloride via The Sulfur Catalyzed Chlorination of Benzaldehyde
Good day all,
I have not had occasion to do any meaningful chemistry as of late, but I will post one of my more successful reactions circa January 2020.
Just from my own notes, extrapolated and explained a bit of course.
Few things before we touch off:
1. Benzaldehyde was purchased (not illegal where I am) from eBay, but it could've easily been made. I used up my home-made and vac distilled batch I
made via Praxyis(sp) aka Doug from Dougs Lab & Tom from Tom's Lab thread on the Nitric acid oxidation of Benzyl Alcohol to Benzaldehyde doing test
runs that failed, but in my opinion the failures had nothing to do with the quality of the benzaldehyde, just my poor temperature control.
http://www.sciencemadness.org/talk/viewthread.php?tid=72076
2. Chlorine was made from the TCCA and HCl dripped method, re: Nurdrage and many others here; I used a 2 molar excess but would use a bit more (2.25 -
2.5 mol excess) in the future as not all reacts even with heating and stirring.
https://www.youtube.com/watch?v=hLHfN7GvAyI
3. I used ordinary garden Sulfur as the catalyst, recrystallized from toluene so it was a shiny, sparkly pure yellow (what a waste of time but I
didn't have another source and I wasn't waiting weeks for eBay).
4. You need a hood, great ventilation or a good 550 CFM fan and 6 inch tubing like I had with my temporary setup to suck out not only unreacted
chlorine, but the HCl gas this generates. It fumes in air, damp night air much more vividly, for the neighbour conscious among us.
I use a 3M mask with Acid cartridges the entire time I do anything like this as backup, but it WILL NOT stop anything but blow-by or
nuisance chlorine vapours so be warned. The chlorine generator, once started, can't be stopped easily in my experience.
Ok, onto the preamble:
Introduction
-----------------
Benzoyl Chloride was Synthesized via the Sulfur Catalyzed Reaction of Chlorine upon Benzaldehyde at Moderate Temperatures.
Read the attached MSDS for Benzoyl Chloride before diving into this one, as it can be pretty toxic and fumes in open air. It's also very lacrimatory.
Spill some on a hot stove or hotplate? Bam you just made PHOSGENE gas.... Be warned!
US Patent 3894923 (Attached below), was used (but kind of not used) as a guide.
What I mean by this is their patent is all about UV light helping the chlorination along, but they give a comparative example at the very bottom using
plain old Sulfur.
Materials & Reagents
--------------------------
312 grams TCCA (Tri-Chlorocyanuric Acid)
500 ml 31.45% Hydrochloric Acid
212 grams Benzaldehyde
0.5 grams Sulfur
CaCl2 for drying tube(s)
Hotplate
Stirbar
Silicone Tubing
1 x 2000 ml 3-neck flat bottom flask
1 x 500 ml 3-neck flat bottom flask
4 x screw-down type thermometer adapters (3 minimum)
1 x 500 ml pressure equalized dripping funnel (or smaller one and be able to add more to it as you go, which is bloody TERRIBLE with a reactor under
pressure making Chlorine)
1 x drying tube
1 x reflux condenser
1 x small aquarium air pump (optional but recommended)
1 x wicked ventilation system or fume hood
Experimental
------------------
To a 3-neck, 500 ml flat bottomed flask was added 2 moles of Benzaldehyde (212 grams), 0.1% of this weight in elemental Sulfur (about 0.5 grams was
used), and a small stir bar.
The flask was then placed on a hotplate, one neck affixed with a thermometer well attached to an electronic thermo-couple, the center neck attached to
a reflux condenser, and the other side neck attached to a thermometer adapter that had a small hollow borosilicate glass tube running through it down
into the stirred benzaldehyde for chlorination. To the top of the reflux condenser was attached a drying tube packed with CaCl2, to prevent water
condensing down into the reaction flask.
The aforementioned glass tube was attached via silicone fish tank style tubing to the chlorine generator, which will now be described:
A 2000 ml flat bottom 3-neck flask was filled with 312 grams of powdered TCCA, the center neck rigged with a 500 ml pressure equalized dripping
funnel. The dripping funnel was filled with a slight molar excess of 31.45% Hydrochloric acid, approximately 500 ml (or about 160 grams of HCl) worth.
More HCl can be added to make swirling this flask easier to ensure all the TCCA reacts.
One side neck of the above mentioned flask was fitted with a hollow 200 mm 24/29 borosilicate glass tube, packed with CaCl2 and cotton-balled at both
ends. This is to ensure the generated chlorine gas is dry. This 200 mm packed drying tube was attached to yet another thermometer screw-down type
adapter and silicone hosing to the reaction flask glass tube to provide the chlorine.
The other and final neck of the flask was fitted with a thermometer adapter, silicone tubing, and that tubing was attached to a VERY tiny aquarium
style pump. This was to keep mild but consistent positive pressure in the chlorine generator to prevent suck-back issues. I tend to do this on every
gas generator reaction I do, especially HCl gas generators, to avoid suck-back. As long as that drying tube is well packed with a suitable drying
agent, it has always worked well.
The 500 ml pressure equalized dripping funnel was filled with 500 ml of 31.45% HCl, and the small aquarium air pump turned on to check the flow,
bubble size and depth into the benzaldehyde from the chlorine generator (at this point it was all just regular room air).
Cold water was now run through the reflux condenser, and the hotplate and magnetic stirring was turned on and a temperature of approx (+/- 5 C) 120
Degrees C was reached. Ventilation was begun (ideally should be on before now as a rule).
The 500 ml HCl was now slowly at first dripped onto the TCCA powder. Immediately a yellow-green chlorine gas haze was seen in the chlorine generator
flask, and chlorine was starting to be piped into the benzaldehyde.
The chlorine generator flask was lifted and swirled occasionally, and as the reaction continued the drip rate was adjusted to provide a steady (as can
be) stream of gas into the reaction flask.
At approximately T + 10 minutes the reaction flask temperature was approximately 135 Degrees C, and the hotplate heating was turned off and passive
air cooling was started. HCl gas was steadily evolving from the top of the reflux condenser, out the drying tube and being sucked out of the lab
space. Litmus paper held above this drying tube turned bright red very quickly.
After approximately T + 1 hour the reaction flask cooled to the point where I stopped the cooling fan, but did not re-start the hotplate.
Around T + 1.5 hours the reaction was approximately 110 Degrees C and the hotplate was cautiously restarted. Litmus paper at the exit drying tube atop
the reflux condenser was still bright red with HCl gas evolution.
Around T + 2.25 hours the chlorine generation began to slack considerably, and the flask was swirled. I placed in on a small pan and used a gas range
to briefly heat the flask, but this was discontinued as it really was not doing much in the way of gas generation. Litmus paper at the exit drying
tube atop the reflux condenser was still bright red with HCl gas evolution.
Around T + 2.5 hours, the entirety of the 500 ml HCl was finished dripping into the chlorine generator. Litmus paper at the exit drying tube atop the
reflux condenser was still bright red with HCl gas evolution.
At T + 3 hours, the reaction flask was approaching 95 Degrees C, the entirety of the HCl was long since added, and litmus paper at the exit drying
tube atop the reflux condenser was no longer instantly turning bright red, indicating the HCl gas evolution from the reaction was slowing and the
reaction was close to completion.
At T + 3.25 hours, I turned off the hotplate, stirring, cooling water, and CAREFULLY disconnected the glass tube feeding the reaction flask with
chlorine (aquarium air pump still on as to avoid any suck-back). I then quickly stoppered the reaction flask and turned off the aquarium air pump to
avoid filling the room with even more HCL and Chlorine gas vapours. The Chlorine generator flask was quenched carefully with water several times and
its contents disposed of.
The contents of the reaction flask were poured into a 250 ml round bottom, affixed with a vigereux column, and set up for vacuum distillation.
Everything was collected until there was a brown tar and what remained of the Sulfur catalyst in the distillation flask. In the collecting flask was
204.4 grams of a clear, slightly syrupy liquid that fumed upon exposure to air. Temperature was approx 210 - 220 Degrees C at the still-head when it
was shut down.
This flask was then setup for fractional distillation at atmospheric pressure. Everything below 197 degrees was discarded (Benzoyl Chloride bp = 197.2
C), and 199.9 grams of clear, colourless liquid was collected. This liquid was slightly viscous and fumed upon exposure to air.
The temperature at collection was very sharp and steady, and the space between fractions very large. Inside the distillation flask was a small amount
of a slightly yellowish clear fluid, which crystallized upon cooling. This was most likely benzoic acid from the atmospheric distillation of whatever
remaining benzaldehyde came over during the vacuum distillation.
The Benzoyl Chloride was poured into a dark glass bottle and stored in the fridge. Depending on what you are using it for, some desiccant may be
advisable for storage.
See attached paper, Cahiez 2001, for a broad overview on storage and handling.
Yield
--------
2 moles Benzaldehyde 212.28 grams = 2 moles Benzoyl Chloride 281.14 grams theoretical yield.
199.9 grams actual yield of Benzoyl Chloride / 281.14 grams theoretical yield = 71.1%
Ergo, the final molar yield was 71.1% on starting Benzaldehyde.
Comments
---------------
As mentioned, without risking di and/or tri-chlorinating the Benzaldehyde, a bit more chlorine could be used. This might get the yield up a bit.
The yield tracks decently from the example in the patent (Their yield was listed as 82%).
Overall I think this worked pretty damn well all things considered. Working with chlorine or any gas really always kind of sucks, especially in an
amateur setting, so I feel this was a great success.
Questions, critiques and comments always welcome!
Cheers~!
Attachment: US3894923 - Sulfur Catalyzed Winner - Copy.pdf (119kB) This file has been downloaded 466 times
Attachment: cv3p0112 - Benzoyl Chloride Purification Ref - Copy.pdf (313kB) This file has been downloaded 424 times ![Purification of Benzoyl Chloride - Copy.png - 34kB](https://www.sciencemadness.org/whisper/files.php?pid=644014&aid=83053)
Attachment: BENZOYL-CHLORIDE MSDS - Copy.pdf (57kB) This file has been downloaded 589 times
*EDIT: Typos, attachments, and flask sizes corrected*
Attachment: cahiez2001 - Benzoyl Chloride Facts - Copy.pdf (77kB) This file has been downloaded 538 times
[Edited on 1-9-2020 by Johnny Windchimes]
[Edited on 2-9-2020 by Johnny Windchimes]
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S.C. Wack
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Have you tried it without S2Cl2 or UV?
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clearly_not_atara
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The reaction works with just BzH + TCCA in CH2Cl2 as in e.g.:
http://doi.org/10.1002/adsc.201500912
http://doi.org/10.1021/acs.orglett.5b01579 (free Supporting Information)
Also reported to work with BnOH but may give some BzOBn.
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S.C. Wack
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The reaction works with just chlorine i.e. neat.
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Tsjerk
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https://www.prepchem.com/synthesis-of-benzoyl-chloride/
See the second preparation
[Edited on 1-9-2020 by Tsjerk]
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Johnny Windchimes
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I should definitely mention, the TCCA DCM Benzaldehyde room temp reaction of which you speak....
I followed the paper precisely. Scaled it up big time of course. But guess what.... it's not that papers lie, it's that scaling doesn't always SCALE
correctly....
5 days later (as per the paper, scaled up x like 100 if I recall as this wasn't even pretending to be preparatory), I distilled off the DCM, at
atmospheric, and as I always wear my 3M Mask as a rule, my life was saved that day.
Last thing I recall was the still-head temp going to about 180 degrees C, and then BOOM.
Vigereux, 3-way, thermometer well, everything blew and it all hit the roof. 1-neck flask in the 2000 ml mantle didn't crack for god knows whatever
reason. The entire lab space was filled with thick white smoke. The condenser was toast. THICK WHITE SMOKE.
I turned off the water, and bumble f*cked my way out of the lab space and up the stairs. White acrid smoke was clearly noticed (and tasted) through my
respirator.
The entire house (thank god its all mine, and isolated-ish) was filled, via the furnace air fan, with this acrid white smoke.
THIS IS WHY YOU SHOULD NEVER DO CHEMISTRY LIKE THIS IN AN APARTMENT OR SHARED
DWELLING.
All the windows were thrown open and whatever emergency ventilation I could muster was turned on. I was very sure I made the target compound before it
blew, hence the white smoke, but couldn't be sure I didn't just make a pile of PHOSGENE GAS.
5 panic attacks later here I am, and all the wiser for it.
I still don't know what touched it off. Too much heat? Contams? Side products reacting? Bad JuJu?.....
I was very lucky, and tell this tale to remind everyone that however much you think you know (and oh I know so very little....), it's never enough to
duck safety precautions.
Which I didn't, and never will. That's why I'm able to type these words this day.
I'll muster a picture or two I took an hour after..... If I can find them..... they make Magpie's "Oleum made UNCONTROLLABLE FUMES" post(s) pictures
look like someone discreetly vaping in a movie theater compared to the toxic cloud of stupid I made that day....
*EDIT* No, never tried UV, or anything like S2Cl2, but was looking into all the literature I could find at the time, and do recall some preps along
those lines.
[Edited on 1-9-2020 by Johnny Windchimes]
[Edited on 1-9-2020 by Johnny Windchimes]
[Edited on 1-9-2020 by Johnny Windchimes]
Attachment: KABOOM - gaspa2015 - Benzoyl Chloride via Benzaldehyde and TCCA - Copy.pdf (508kB) This file has been downloaded 698 times
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Johnny Windchimes
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Post Script :
Your article's almost the same as mine..... Gaspa essentially posted it twice with minor albeit significant changes..... Even the wording is the
same....
Wonder if your version KABOOMs too? I won't be trying it out to see....
Like, it's a carbon copy with chemicals sub'd in.... spooky actually....
Attachment: gaspa2016 - Copy.pdf (406kB) This file has been downloaded 458 times
Attachment: KABOOM - gaspa2015 - Benzoyl Chloride via Benzaldehyde and TCCA - Copy.pdf (508kB) This file has been downloaded 661 times
[Edited on 2-9-2020 by Johnny Windchimes]
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clearly_not_atara
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Well, the good news is you didn't make phosgene. You had already distilled off the DCM when the explosion occurred; if there was any phosgene, you'd
be dead.
The bad news you already know. One key safety precaution: always start small!
Quote: | I still don't know what touched it off. Too much heat? Contams? Side products reacting? Bad JuJu? |
TCCA itself is potentially unstable: the reaction C3O3N3Cl3 >> 3/2 Cl2 + 3/2 N2 + 3 CO is already exothermic with deltaH = -210 kJ/mol!
So it is not a good idea to heat mixtures containing TCCA, DCCA or MCCA. All three can decompose violently. The stated thermal decomposition
temperature of TCCA is 225 C from the MSDS:
http://www.wisdah.com/imgs/2018/10/MATERIAL-SAFETY-DATA-SHEE...
With "catalytic crud" this could happen at 180. Since the BP of BzCl is 197 C I conclude that BzCl produced by this method can not be
distilled safely at atmospheric pressure.
[Edited on 1-9-2020 by clearly_not_atara]
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Well, I'd think that would be the point of hot S + Cl, although the older directions call for cold no-S.
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Johnny Windchimes
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Quote: Originally posted by clearly_not_atara ![](images/xpblue/lastpost.gif) | Well, the good news is you didn't make phosgene. You had already distilled off the DCM when the explosion occurred; if there was any phosgene, you'd
be dead. |
Yes indeed. I wasn't intending on posting that 'failure', (if such a brush with the afterlife can be such ascribed to...), but when that Gaspa article
was posted I felt hurriedly compelled to do so.
I am clearly not the best chemist, nor do I pretend to be, but I would certainly lose sleep knowing that if someone Googled 'Benzoyl Chloride', they
would look and think, as I did, "boy this Gaspa article is way easier, if not a bit time consuming", and trod down that path as blindly as I did.
Again, it's not Gaspa's fault, it's mine, scaling up a procedure from millimoles to mole'y moles.....
Learn from this is all I ask, if anything at all....
[Edited on 2-9-2020 by Johnny Windchimes]
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Johnny Windchimes
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If memory serves, I didn't try the UV initiated version(s) of this synthesis because my mercury vapour HID lamp, that I in no way had lying around
from the old veg cycle of growing the devils lettuce, was pooched from me dropping it onto concrete....
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Tsjerk
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Well, it wouldn't have made sense to try the UV anyway because the reaction runs without a catalyst with nearly quantitative yield.
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clearly_not_atara
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Quote: Originally posted by Johnny Windchimes ![](images/xpblue/lastpost.gif) | Quote: Originally posted by clearly_not_atara ![](images/xpblue/lastpost.gif) | Well, the good news is you didn't make phosgene. You had already distilled off the DCM when the explosion occurred; if there was any phosgene, you'd
be dead. |
Yes indeed. I wasn't intending on posting that 'failure', (if such a brush with the afterlife can be such ascribed to...), but when that Gaspa article
was posted I felt hurriedly compelled to do so. |
As far as I can tell, nothing actually went wrong during the rxn procedure itself.
The other lesson is to learn about the reagents you use, even "normal" ones like TCCA. I doubt you would have tried a thermal distillation if you had
known the decomposition temperature beforehand.
Gaspa's procedure is fine; heating TCCA to 200 C is not fine.
EDIT: I've been quite stupidly lazy here. I should have posted the actual procedure:
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b01579/s...
TCCA (55 mmol) was portionwise added over a period of 1-2 minutes into a solution of benzaldehyde (55 mmol) in 162.5 mL dichloromethane
under Ar atmosphere and at room temperature. The resulting suspension was stirred at room temperature for 5 days under Ar (the reaction was
monitored by TLC until disappearance of aldehyde). Aliquot was analysed with HPLC (CH3CN, flow rate 1 mL/min, Pressure 380 PSI, injection
volume20 μL, t. R 3.899) and compared with the chromatogram of standard (benzoyl chloride obtained by commercial source). The mixture of reaction was
filtered on Celite, then the solvent was removed under vacuum and the residue was distilled. 1H NMR (400 MHz, CDCl3) δ : 8.08 (d, J= 7.8 Hz, 2H),
7.66 (t, J= 7.4 Hz, 1H), 7.48 (t, J= 7.6 Hz, 2H).13C NMR (100 MHz, CDCl3) δ : 168.3, 135.4, 133.2, 131.4, 129.0.
But really I should also have known myself to warn about TCCA decomposition.
[Edited on 3-9-2020 by clearly_not_atara]
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Johnny Windchimes
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Quote: |
Again, it's not Gaspa's fault, it's mine, scaling up a procedure from millimoles to mole'y moles..... |
Can't be overstated. For myriad reasons, not just the scaling.
Solubility in DCM aside, I should point out I did vac filter off the very insoluble unreacted TCCA / reaction mixture to be left with a crystal clear
yellow liquid before distilling it.
Definitely helped it go down from ultra lethal hand grenade type explosion to just a garden variety horrifyingly scary accident I would wager....![:o](./images/smilies/shocked.gif)
@Tsjerk, I started experimenting with the simplest method(s) I could find, and could not for all my 'skill' get the catalyst
free reaction(s) to run properly. 10.... 20 percent yields tops. Very frustrating at the time, so I looked into alternatives like Gaspa.
[Edited on 3-9-2020 by Johnny Windchimes]
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SplendidAcylation
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Great write-up!
I have carried out this procedure myself, and I found it to be surprisingly "easy" despite having to deal with chlorine gas.
I am planning to try it again on a larger scale, and I was wondering if I need to use such a large excess of TCCA?
The first time I did it, I also used a large excess of TCCA, but I really don't want to waste it, especially on a larger scale.
I have seen many procedures and write-ups where it is claimed that the yield of chlorine from TCCA is almost quantitative...
Indeed, if I use an excess of acid, this will ensure all of the TCCA is consumed, and any excess acid might be recovered by distillation.
If anyone is reading this who has used TCCA to generate chlorine, what sort of excess would you use?
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clearly_not_atara
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For comparison:
http://orgsyn.org/demo.aspx?prep=cv1p0155
Note that the o-chloro makes the reaction much slower because it aldehyde is more resistant to oxidation.
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SplendidAcylation
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Thanks for the response!
I guess I'll just have to use a conservative quantity of TCCA, and add more if necessary, dealing with the inevitable escape of chlorine from the
flask when I have to open it to add new TCCA ![:D](./images/smilies/biggrin.gif)
Yes I can see the reaction of the o-chloro substituted aldehyde is a lot slower, I think when I first did this reaction using benzaldehyde, it only
took around three hours.
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SplendidAcylation
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How problematic is dissolved HCl in acyl halides?
Hi,
I have since attempted the chlorination of benzaldehyde to make benzoyl chloride, and it was quite successful, the chlorination itself was the most
fun I've had in years! ![:P](./images/smilies/tongue.gif)
However there is a problem, and I am wondering if anyone has a suggestion as to how I should progress;
My benzaldehyde was prepared by the oxidation of benzyl alcohol using nitric acid.
Unfortunately, it is likely that it contained some unreacted benzyl alcohol (I did not know this earlier).
I then carried out the chlorination, and distilled the product.
I collected benzoyl chloride from 194-202c, whereupon a fraction of benzyl alcohol began to distill over up to 206c.
After that, nothing more distilled, however a fairly large quantity of viscous, tarry liquid remained in the distilling flask.
During the distillation, a lot of hydrogen chloride gas was evolved.
"Wait a second", I hear you say, "How could benzyl alcohol and benzoyl chloride possibly coexist?"
I suspect that when the mixture of benzyl alcohol and benzaldehyde was chlorinated, the benzaldehyde reacted, forming benzoyl chloride, but the benzyl
alcohol would remain unchanged.
Since the reaction between acyl halides and alcohols is quite slow, they would not have reacted straight away, but heating to distill the product
would have resulted in a lot of the benzyl alcohol reacting with benzoyl chloride, forming benzyl benzoate, which is probably the viscous high-boiling
liquid left in the distilling flask.
I attempted to vacuum-distill the viscous stuff, but it required too high a temperature, given my vacuum setup.
So anyway, the problem is, I have a clear distillate consisting mainly of benzoyl chloride, however it may contain some benzyl alcohol too.
Since the reaction between benzyl alcohol and benzoyl chloride is slow, it may not immediately esterify.
If I were to carry out a second distillation, I would be able to distil off the benzoyl chloride, however doing this might produce more hydrogen
chloride by the reaction of benzyl alcohol with benzoyl chloride.
Alternatively, I could reflux my product, which would ensure that all of the benzyl alcohol reacts, however I am wary about doing this, because
perhaps refluxing benzoyl chloride will result in some loss due to polymerization, etc?
In any case, it might be a good idea to pass dry air through the benzoyl chloride to remove dissolved hydrogen chloride.
Tl;Dr:
My benzoyl chloride might be contaminated with benzyl alcohol, and it might also contain some dissolved HCl.
How big of a problem is dissolved HCl in acid halides, is it even soluble in them?
I imagine that every time you open a bottle of an acid halide, some water will get in, resulting in the formation of hydrogen chloride, which would
surely dissolve in the acid halide...
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clearly_not_atara
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I think that the solubility of HCl in BzCl is probably quite low. HCl is highly volatile and only dissolves in solvents by dissociation. But the
basicity of BzCl is certainly low, probably lower than that of BzOH, so the pKa of HCl in BzCl is probably higher than 3.
But if BnOH is present then it can react to BnCl, and if BzOBn is present then it can be protonated.
Samples of acyl chlorides are rarely rigorously pure. If you distill it and the residue is not very much, it should be clean enough for most practical
purposes. I don't think it polymerizes very easily.
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SplendidAcylation
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Quote: Originally posted by clearly_not_atara ![](images/xpblue/lastpost.gif) | I think that the solubility of HCl in BzCl is probably quite low. HCl is highly volatile and only dissolves in solvents by dissociation. But the
basicity of BzCl is certainly low, probably lower than that of BzOH, so the pKa of HCl in BzCl is probably higher than 3.
But if BnOH is present then it can react to BnCl, and if BzOBn is present then it can be protonated.
Samples of acyl chlorides are rarely rigorously pure. If you distill it and the residue is not very much, it should be clean enough for most practical
purposes. I don't think it polymerizes very easily. |
Thanks for the reply!
It had never occurred to me that the solubility of HCl is due to dissociation, but it makes sense of course!
I tried converting some of my benzoyl chloride to acetyl chloride by distilling it with acetic acid, and I obtained a 60% yield, so I am quite pleased
with this result...
The residue, consisting mainly of benzoic acid, contained some unreacted benzaldehyde, which must have been present in the benzoyl chloride due to
incomplete chlorination; Still, it doesn't seem to have been a problem ![:)](./images/smilies/smile.gif)
As a side note: If anyone makes benzoyl chloride and thinks "oh this isn't too reactive", this behaviour isn't typical of acyl chlorides, as I
discovered to my detriment after preparing acetyl chloride, whereupon I was met with clouds of hydrogen chloride gas upon merely opening the receiving
flask!
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