| Pages:
1
2 |
Organikum
resurrected
Posts: 2337
Registered: 12-10-2002
Location: Europe
Member Is Offline
Mood: frustrated
|
|
I guess no NaCl is used for the chloroacetone wont like the formed NaOH very much and for electrolysis under basic conditions favors the production of
oxygen over the production of chlorine and we want to chlorinate not to oxidise the acetone.
A molar excess of acetone will be a good idea if monochloroacetone is what one is after. Anyways it is favorable to stop the electrolysis long before
the reagents are used up completely for to avoid overchlorination.
All reagents have to be distilled - in special the HCl if not labgrade HCl is available. Muriatic acid is highly contaminated with metalsalts which
cause polymerisation faster than you can spell the word "tar". Light also causes polymerisation.
After the reaction the monochloroacetone is withdrawn from the bottom - nice to have a faucet there - cooled down and neutralized by chalk, filtered
through glasswool and stabilized by some chalk agsin and stored COLD in a DARK glassbottle.
If you skip the coling down before or whilst neutralizing the HCl you will cry a lot. If cooled you will cry too but not so much at all.
Wear swimming googles. 
|
|
|
TheBear
Hazard to Self
Posts: 78
Registered: 17-10-2002
Location: Sweden
Member Is Offline
Mood: distilled
|
|
| Quote: | | Wear swimming googles. |
LOL, imagine a neighbour seeing me..  I would love to see the looks of their
faces. Distilling HCl acid: Then I guess this will have to wait until a somewhat proper fumehood is built, or perhaps 2 washing bottles could remove
the problem, washing bottle 1 = H2O, 2 = Na2CO3 (aq).
Anyway I will have to improvise the apparatures. What concentration of the reagents should be used? HCl in excess that I understand, but acetone, 20%
by weight or is that to much/less?
|
|
|
Organikum
resurrected
Posts: 2337
Registered: 12-10-2002
Location: Europe
Member Is Offline
Mood: frustrated
|
|
A neighbour crying his eyes out because of chloroacetone - this will bring you in serious trouble man, my word on this.
Excess HCl - I didnt tell this - did I?
Distilling HCl is no problem. HCl forms an azeotrope with water at 20% which boils at 108°C. So if you dilute your muriatic shit down to 20% or less
you can distill the HCl like water - no problem, no fumes no hassle.
20% acetone w/w is not enough I guess, hey - do the math yourself I dont like to do these calculations either!
|
|
|
TheBear
Hazard to Self
Posts: 78
Registered: 17-10-2002
Location: Sweden
Member Is Offline
Mood: distilled
|
|
You misinterpretrated my post, I am by no means asking you to do the calculations for me, I only need a approximation on how concentrated the
reactants should be in the water, since i have no idea I could think of anything between 1% and 80%. Anyways, if chloroacetone is so unpleasant is
there anything else commonly avaible to chlorinate which would give a more easily handled product, etylalcohol?
I'm not really after chloroacetone I'm only interested in trying chlorination through electrolysis..
I feel like I want to appologise if I sounded ignorant which wasn't my intention.
EDIT: Regarding HCl, I don't know why I thought of using it in execss, but it shouldn't hurt? but rather make sure the speed of
electrolysation does not stagnate?
[Edited on 23-4-2004 by TheBear]
[Edited on 23-4-2004 by TheBear]
|
|
|
MEXCHEM2006
Hazard to Self
Posts: 50
Registered: 22-8-2006
Location: MEXICO
Member Is Offline
Mood: No Mood
|
|
You can make chloroacetone with SO2Cl2 in metanol/methylene chloride solution in a 85% yield , if you do electrolysis you would get a mixture of
chloroacetones.
|
|
|
DDTea
National Hazard
Posts: 940
Registered: 25-2-2003
Location: Freedomland
Member Is Offline
Mood: Degenerate
|
|
| Quote: | Originally posted by MEXCHEM2006
You can make chloroacetone with SO2Cl2 in metanol/methylene chloride solution in a 85% yield , if you do electrolysis you would get a mixture of
chloroacetones. |
You take the fun out of it! 
There is always a 'standard' way to prepare such compounds, and Chloroacetone is by no means a challenge to an equipped lab. But this now begs the
question: where do we get SO2Cl2? How does one construct such a reaction vessel to handle that?
I'm revisiting this thread because I'm seeing more and more uses for Chloroacetone--it's such a basic (simple, not low pH) compound--that can be used
to construct far more interesting compounds. It is therefore of much interest to be able to produce it cheaply from OTC precursors and ghetto
reaction cells easily procured by the amateur
Alpha Substitution opens the door to a whole wonderland of compounds! Ah looking back three years ago, I had such tunnel vision to just see
Chloroacetone as a lachrymator and tear gas...don't get me wrong: first thing I do to confirm its presence is to sniff it Then I might run a TLC and all that other more professional rod-up-the-ass
white-coat-buttoned-too-tight stuff 
Now don't get me wrong, SO2Cl2, SOCl2, POCl3, and other wonderful chlorinating agents are truly invaluable in organic chemistry and unless home
chemists can acquire them, they really do face brick walls when they aspire to reach higher goals. No doubt, we'll have to break down those walls
eventually.
I've been sitting on my arse entirely too long.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
|
|
|
garage chemist
chemical wizard
Posts: 1803
Registered: 16-8-2004
Location: Germany
Member Is Offline
Mood: No Mood
|
|
SO2Cl2 is different from SOCl2 in that is significantly easier to prepare: react gaseous SO2 with gaseous Cl2 with active charcoal as catalyst (no
heating of the catalyst tube required, reaction creates its own heat). NaturesNatrium has done it, but he doesn't seem to be around here much lately.
|
|
|
MEXCHEM2006
Hazard to Self
Posts: 50
Registered: 22-8-2006
Location: MEXICO
Member Is Offline
Mood: No Mood
|
|
I made this reaction before; you fill the bulbs from a bulb condenser with a little fiberglass and then some activated charcoal, leave a little space
between the bulbs, pass a DRY gaseous (constant) stream of SO2 and Cl2 from upper part of the condenser thru the condenser, the activated charcoal
will start to absorb the gases and half an hour later you will have liquid SO2Cl2 coming out of the condenser.
|
|
|
new-b
Harmless
Posts: 15
Registered: 12-2-2006
Member Is Offline
Mood: No Mood
|
|
Could it be possible to obtain 1,3-dichloroacetone with the SO2Cl2 method? Do you have more informations about this method? Thank you.
|
|
|
HOLYMOLYBDENUM
Harmless
Posts: 3
Registered: 10-4-2013
Member Is Offline
Mood: No Mood
|
|
Quote: Originally posted by Organikum  |
A molar excess of acetone will be a good idea if monochloroacetone is what one is after. Anyways it is favorable to stop the electrolysis long before
the reagents are used up completely for to avoid overchlorination.
After the reaction the monochloroacetone is withdrawn from the bottom - nice to have a faucet there ...
|
I can't imagine that there would be separately visible layers between the chloro/acetone layers whilst in this vessel, would there? The chlorinated
product is obviously denser, sure, but how could the two compounds be viably separated in that manor if they look identical?
|
|
|
Metacelsus
International Hazard
Posts: 2539
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
I just did the electrolysis with 1 part acetone to 1 part 37% HCl using graphite electrodes. I got a mixture of mono and dichloroacetone with aldol
tar. The dichloroacetone formed as an oily brown layer on the bottom; the color is probably due to aldol products. I estimate my yield of
monochloroacetone was about 30%, but I haven't finished purifying the product; I'm having trouble getting all the water out.
[Edited on 11-4-2013 by Cheddite Cheese]
|
|
|
Mildronate
Hazard to Others
Posts: 428
Registered: 12-9-2009
Member Is Offline
Mood: Ruido sintetico
|
|
can you write it more detailed? Current, electrodes dimensions, how you know that is chloroacetone?
|
|
|
Metacelsus
International Hazard
Posts: 2539
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
The current was 5A; the current density was about 0.2 A/cm^2. When I purified it by distillation, its boiling point was 118 C, and its final density
was 1.1 g/cm^3. The final yield of pure product was quite low: only 9%. I believe this to be because of aldol condensation and the production of
polychlorinated acetone, and mechanical losses in purification (damn tar!). When freshly distilled, it was clear, but it has slowly yellowed over
time.
Also, I know it to be chloroacteone because of its effects on my eyes -- I had to wear swim goggles to even enter the garage, which is where my
electrochemical cell was.
If I do it again, I will use a platinum anode to improve efficiency, and also try to keep the cell temperature down. It rose to about 50 C because of
ohmic heating.
[Edited on 11-10-2013 by Cheddite Cheese]
|
|
|
| Pages:
1
2 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
