The hypoflourite ion does exist. (hypoflorous acid is in fact the only solid-state stable hypohalous acid) The problem with fluorine lies in the fact that the haloform reaction mechanism reguires a partial positive charge on the halogen, but fluorine is so electronegative that it has a partial negative charge in the oxygen to fluorine bond.
You would have gotten a much higher yield if you let the liquid in the jugs settle longer. The turbidity in the first 3 liters that you decanted down the drain was due to suspended chloroform, so you lost a lot of chloroform by decanting those down the drain.
thing is, the water has a large amount of salts in it so the difference in densities is much smaller. This makes the dispersion settle much slower than one might expect. Might be better had he left it overnight or something.
@@conquereroftheuselessI wondered why this advice wasn’t given. However, considering that chloroform is often used as a solvent in very specific conditions, how would you separate ethanol from the chloroform? One would need to be prepared to wash with water to preferentially remove the ethanol while losing some chloroform. Instead, we could store chloroform below a layer of sodium carbonate in water (which removes and deactivates the phosgene), the water you’d need to wash the chloroform anyway. It should be stored upright in an area with stable temperature and a lid that allows pressure to escape.
@@SetTheCurve got your point. If I need chloroform in a pure way I would synthesis it right away and use the fresh one. But your process is fine too :)
@@SetTheCurvethe problem with this is that water hydrolyzes the chloroform over time. Ethanol stabilized chloroform is fine for most reactions anyway.
Hey, I was wondering if you wanted to try extracting caffeine from something using chloroform. Caffeine is twice as soluble in chloroform than in dichloromethane. You have a fume hood so the fumes from boiling off shouldn't be an issue.
Doug man, you still with us amongst the living? Haven't heard from ya in a while. Hope you didn't have an unfortunate lab accident. I could see not making YT video esp with YT's rules and algorithms. But man let us know if your still alive!
Try freezing out the CHCl3 from the waste aqueous phase. Freeze until about half frozen. Pour off liquid. Ice should be pure water. Some CHCl3 should be in liquid phase. Phase separate out the CHCl3. Combine aqueous phases. Repeat. Keep repeating until no more CHCl3 is obtained. Report yield in another TH-cam video.
I understand Phosgene is extremely hazardous. however after a great deal of research I cant seem to find a whole lot of information about chloroform degrading to phosgene in the lab causing significant problems. I wonder if its mostly large scale operations that suffer the most.
You have a severe lack of subscribers. Maybe see if you can do a collaboration with Cody's Lab or Nile Red, it could help you gain some traction :P Love your channel, keep it up.
If you've never done this reaction, do not for one second assume the large mass of water will be enough to absorb the reaction heat. It will not. This reaction really puts out an unbelievable amount of heat. Don't ask me how I know.
yeah even pre-chilled solution at -10 °C or almost freezing up is not enough to absorb all the heat - the best way is to add the acetone slowly, with stirring and cooling - this should be a best practice for any such exothermic reactions
Doug, you should have let the water chloroform mix sit longer so it would fully settle. dont let it settle too long since the sodium hydroxide produced will eventually react with the chloroform to make sodium hypochlorite
Just struck me odd thinking about the nasty carcinogenic tendencies of chloroform. Replace two of the Cl's with Fluorine gives R-22 (Chlorodifluoromethane) which is supposedly harmless. Chloroform is an interesting molecule particularly when oxidized.
The best way i saw to do this, and u can get close to quantitative amounts, even doing all three gallons, was to use a 10 gallon bucket, a whole bag of ice, like store bought bag, pour jnto bucket, then bleach, then your 130ml of acetone or MEK, stirring constantly, another bag of ice nearby, just incase. As u stir it goes cloudy, ice even gets smaller. But it slows the warming after 30 or so minutes, ice cubes are very melted, but still there. Pour in more ice, not necessary to dump whole bag, maybe half a bag. U can leave the area and live life... come back a few hours later, even doing this setup at night, sleeping after temperature rising has plateaued or at least appears to, after 20-30min. Next morning using an oral syringe or turkey baster (jve used nasal suckers for babies to siphon before) suck out the chcl3 and put into amber bottle, store in cool, dark place, capped.
I have seen about a hand full of Chloroform, but never Chloral Hydrate. also from what I understand Chloroform decomposes fairly quickly, and after a night or so you can pour the excess material down any drain. you can also push this along by adding a little Lye/Sodium Hydroxide to the mixture.
CHCl3 accumulates in the environment. About 4 cubic millimeters per cubic meter is the atmospheric concentration now. X-planes why people are walking around half asleep.
Can you add a reducing agent to the waste water to destroy the traces of chloroform? Shouldn't you add alcohol to chloroform to prevent forming phosgene? I had a bottle of chloroform (pure, no stabilizers added) polymerize solid and crack the bottle after many years storage. It looks like set epoxy. Have you ever heard of this?
You were dumping water with chloroform in it down the drain. is there a way to treat the waste water to break down the chloroform to a more innocuous substance?
let it stand with aq. NaOH/KOH - it decomposes over time to a less harmful dichlorocarbene another option is to distill the residual CHCl3 off, but this is time/energy consuming
Yes, use water with it, and sodium carbonate/bicarbonate to convert it to sodium hypochlorite, and be VERY wary of the exotherm. It can get out of hand incredibly easily.
FO^- can't exist to my knowledge because of the electronegativity of fluorine being higher as the electronegativity of oxygen - so you should be correct
Is it possible you are adding too much acetone? Unless your jugs are not regular 3.6 litre ones and your concentration is different than 6%, then it seems so. For every 3.6 litre jug you should add 75 ml of acetone if it is 6% bleach. That is what I calculated anyways. I would do 70 because acetone and chloroform cause an azeotrope and then your chloroform would be contaminated with acetone, which would be very hard to remove, so a little less is good. I could be wrong, because your percentage is probably higher than 6%, may be 10? Just curious, I am sure you know what you are doing. Its actually just for my info if I calculated correctly lol. Great video - keep them coming.
As Doug mentioned the reaction is finished if the green color of the chlorine swaps to colorless. Too much aceton is problematic because aceton boils earlier (56 celsius) than chloroform (61 celsius). Aceton dissolves in Water so it is not cost efficient to destill it out. Be carefull !
can anyone help me appreciate it already: the doubts are to boil the sanitary water would increase the concentration of sodium hypochlorite? or you can also use the pool of sodium hypochlorite? and move these measures 1/50 to half and half what happens ???
I tried it with 1 liter bleach bottle and 15 ml acetone, didn't cool in freezer but did the reaction in ice bath, left it over night (I sealed the bottle so it was under pressure when I opened it) and ... nothing. No chloroform layer at all. Can somebody explain what I did wrong?
Bad idea. It is carcinogenic. That is why they stopped using it for an anesthesia. Better to work to the point of exhaustion. Then no problem going to sleep.
Love the vids man. Wanted to ask: I watched your vid on the dean stark apparatus and it got me wondering whether you couldn't use that to separate the water from the chloroform? Am kinda on the fence about it, because increased temp. typically means increased solubility (so the hot mixture may just end up dissolving more chloroform into the water, even in the trap), but then again, I'm no expert on all this, which is why I watch these videos. Feel like they fill in the gaps from all the main 'takeaways' I ended up missing in my chemistry education... lol
Michael Chauncey I agree. I've used calcium hypochlorite and it uses up a lot less space. It just requires a lot more care because everything is a lot more concentrated and it runs away a lot easier. Ice cold efficient condenser is a must.
Try steam distilling the waste aqueous phase. The CHCl3 is more volatile, so it should all come over before much water is distilled over. A three neck distilling flask should be used to speed the process. Rig one arm to siphon off the spent aqueous phase. Use an addition funnel to input more waste aqueous phase. Save overhead aqueous phase for recovery by re-distilling. Report results/yield in future TH-cam video.
basic common lab knawledge. if chloroform was the movie-stuff we wouldn't use it in labs, too dangerous. Looking into anesthesia from ye olden days, they used to soak a handkerchief in chloroform and drape it over the patients face for about 20 minutes. then hope that the patient wasn't anesthetized to death. havnt found how they brought them back, but i suspect fresh air and or ammonia gas like with hartshorn.
+TheZabbiemaster There are a few old documentaries on TH-cam about this topic if you are interested. I was just joking about the whole experience thing.
![[LIVE] : ONE ลุมพินี 89 | คู่เอก "ยอดไอคิว vs คิริลล์"](http://i.ytimg.com/vi/Z3vYkHJ_5Ig/mqdefault.jpg)
my go to chemist
doug's lab, cody's lab, nurdrage, and nile red...thanks for making me feel smartz
Chem player?
omg me too
The hypoflourite ion does exist. (hypoflorous acid is in fact the only solid-state stable hypohalous acid) The problem with fluorine lies in the fact that the haloform reaction mechanism reguires a partial positive charge on the halogen, but fluorine is so electronegative that it has a partial negative charge in the oxygen to fluorine bond.
it always fascinated me that because of this, fluorine reacts with things that have been already oxidized, like being able to burn the ashes
You would have gotten a much higher yield if you let the liquid in the jugs settle longer. The turbidity in the first 3 liters that you decanted down the drain was due to suspended chloroform, so you lost a lot of chloroform by decanting those down the drain.
thing is, the water has a large amount of salts in it so the difference in densities is much smaller. This makes the dispersion settle much slower than one might expect. Might be better had he left it overnight or something.
Always add 1 w% ethanol to stabilise/prevent phosgene build-up if you're going to store it.
aga Thansk for the tip
Excellent advise!
Phosgene is what prevents me from feeling comfortable storing it. Even with the ethanol stabiliser
@@BeastM140i Once you can make the stuff, better not storing it all - just make some when you need it.
@@JohnWalton_NET Nope.
WARNING! You have to stabilize the Chloroform if you wanna store it for a long time
...by adding a tiny amount of Ethanol for example :)
@@conquereroftheuselessI wondered why this advice wasn’t given. However, considering that chloroform is often used as a solvent in very specific conditions, how would you separate ethanol from the chloroform? One would need to be prepared to wash with water to preferentially remove the ethanol while losing some chloroform. Instead, we could store chloroform below a layer of sodium carbonate in water (which removes and deactivates the phosgene), the water you’d need to wash the chloroform anyway. It should be stored upright in an area with stable temperature and a lid that allows pressure to escape.
@@SetTheCurve got your point. If I need chloroform in a pure way I would synthesis it right away and use the fresh one. But your process is fine too :)
@@SetTheCurvethe problem with this is that water hydrolyzes the chloroform over time. Ethanol stabilized chloroform is fine for most reactions anyway.
I like your down to earth style of providing the information. I enjoy watching your videos of chemistry the most. Cheers
You really deserve more Subscribers...
Very informative! Finally someone who explains the chemistry behind it all.
The cloudiness when decanting may suggest you didn't let it settle for long enough.
Also I'm not sure if you already have a video on it, but you should do a video on how to clean your glassware.
Dougs dating "cologne" is super effective ..
topkek!
Hey, I was wondering if you wanted to try extracting caffeine from something using chloroform. Caffeine is twice as soluble in chloroform than in dichloromethane. You have a fume hood so the fumes from boiling off shouldn't be an issue.
Best video on this I've seen. No BS. Kudos
Thank you for helping me prank my whole school they slept for 1 hour
12:53 thats pretty cool. I really like watching the vapor front creep up and over
would salt in the final decanted water not help to force chloroform out of the aqueous layer? Maybe this could be faster and get a better yield?
hypofluoric acid was synthesised at very low temperature, but I don't know about the anion. Thanks for your videod!!!!
Doug man, you still with us amongst the living? Haven't heard from ya in a while. Hope you didn't have an unfortunate lab accident. I could see not making YT video esp with YT's rules and algorithms. But man let us know if your still alive!
Try freezing out the CHCl3 from the waste aqueous phase. Freeze until about half frozen. Pour off liquid. Ice should be pure water. Some CHCl3 should be in liquid phase. Phase separate out the CHCl3. Combine aqueous phases. Repeat.
Keep repeating until no more CHCl3 is obtained. Report yield in another TH-cam video.
Getting anything higher than 25% is much more difficult.
You need a dripper to get just 75% concentrate.
You'll need to do it 2 or 3 times as well.
could you have used some anhydrous epsom salts or CaCl2 to dry in the distillation? - Great method on the bottles though - mesmerising to watch!
I understand Phosgene is extremely hazardous. however after a great deal of research I cant seem to find a whole lot of information about chloroform degrading to phosgene in the lab causing significant problems. I wonder if its mostly large scale operations that suffer the most.
You have a severe lack of subscribers. Maybe see if you can do a collaboration with Cody's Lab or Nile Red, it could help you gain some traction :P Love your channel, keep it up.
If you've never done this reaction, do not for one second assume the large mass of water will be enough to absorb the reaction heat. It will not. This reaction really puts out an unbelievable amount of heat. Don't ask me how I know.
yeah even pre-chilled solution at -10 °C or almost freezing up is not enough to absorb all the heat - the best way is to add the acetone slowly, with stirring and cooling - this should be a best practice for any such exothermic reactions
Doug, you should have let the water chloroform mix sit longer so it would fully settle. dont let it settle too long since the sodium hydroxide produced will eventually react with the chloroform to make sodium hypochlorite
No. 3NaOH +CHCl3 ---> 3NaCl + CHOOH.
Followed by
NaOH + HCOOH ---> HCOONa + H20
Its about time and this channel will be huge thank you doug
Just struck me odd thinking about the nasty carcinogenic tendencies of chloroform. Replace two of the Cl's with Fluorine gives R-22 (Chlorodifluoromethane) which is supposedly harmless. Chloroform is an interesting molecule particularly when oxidized.
The best way i saw to do this, and u can get close to quantitative amounts, even doing all three gallons, was to use a 10 gallon bucket, a whole bag of ice, like store bought bag, pour jnto bucket, then bleach, then your 130ml of acetone or MEK, stirring constantly, another bag of ice nearby, just incase. As u stir it goes cloudy, ice even gets smaller. But it slows the warming after 30 or so minutes, ice cubes are very melted, but still there. Pour in more ice, not necessary to dump whole bag, maybe half a bag. U can leave the area and live life... come back a few hours later, even doing this setup at night, sleeping after temperature rising has plateaued or at least appears to, after 20-30min. Next morning using an oral syringe or turkey baster (jve used nasal suckers for babies to siphon before) suck out the chcl3 and put into amber bottle, store in cool, dark place, capped.
Wow! Now I see why chloroform is so expensive from the lab supply! This was about 40 bucks for that little bit of liquid.
Build more tubes!
I have seen about a hand full of Chloroform, but never Chloral Hydrate. also from what I understand Chloroform decomposes fairly quickly, and after a night or so you can pour the excess material down any drain. you can also push this along by adding a little Lye/Sodium Hydroxide to the mixture.
CHCl3 accumulates in the environment. About 4 cubic millimeters per cubic meter is the atmospheric concentration now. X-planes why people are walking around half asleep.
Awesome. I wish you could show some "Easy destilation, like fractional " I never got that. I'm 58 and I love to learn from you man. Cheers from Sweden
How would one synthesize CCl2F2 from Dichloromethane?
Hi! How can you neutralize the chloroform left in the water before discarding it?
Hydrolyse with aqueous NaOH/KOH, either let stand for a while or if you’re in a hurry reflux
@@lukestyles768 what are the byproducts?
Davide De Rosa NaCl/KCl and Formic Acid
@@lukestyles768 thank you. I expected that (via chlorocarbene intermediate) but I couldn't find a source to check.
would you add anything to it to stabilize it against forming phosgene?
Great video. What is the ratio of NaOCl and acetone? I want to do it with NaOCl at 14 %.
Can distillation be done in a stainless steel/copper vessel?
Would you add ethanol to help stabilize it or not? Also would keeping it in the refrigerator help it or not?
Yes, add a small amount of ethanol and storing in a refrigerator is not a bad idea either.
Can you add a reducing agent to the waste water to destroy the traces of chloroform? Shouldn't you add alcohol to chloroform to prevent forming phosgene?
I had a bottle of chloroform (pure, no stabilizers added) polymerize solid and crack the bottle after many years storage. It looks like set epoxy. Have you ever heard of this?
Could you use a solution of 80%Sodium chlorite 20%sodium chloride and acetone?
Yes.
@@michael636336 thanks
Who would have ever thought that trichloromethane could ever stand in for dichloromethane...? e_e"
What did you use the chloroform for?
+Brian Johnson Don't act like you don't know ( ͡° ͜ʖ ͡°)
Kidnapping kids
😀😀
its a wonderful solvent
You were dumping water with chloroform in it down the drain. is there a way to treat the waste water to break down the chloroform to a more innocuous substance?
let it stand with aq. NaOH/KOH - it decomposes over time to a less harmful dichlorocarbene
another option is to distill the residual CHCl3 off, but this is time/energy consuming
I like to see some another metal so how can I contact you
could one use calcium hypochlorite for this reaction?
Yes, use water with it, and sodium carbonate/bicarbonate to convert it to sodium hypochlorite, and be VERY wary of the exotherm. It can get out of hand incredibly easily.
In the separatory funnel, you mentioned the top layer is water, what happened to the Acetic Acid being formed?
Acetic acid reacts via the haloform reaction to CHCl3 and CO2.
11.5l makes 300 ml?
Why does my bleach turn brown every time I try ?
can trichloroethane b made from chloroform?
I’ve tried making some chloroform this way but the chloroform that separates out is a dark straw colour, any ideas what’s happening?
Hi, can you please make a video on the synthesis of benzyl methyl ketone via chloroacetone and benzene? Thanks!
choloacetone (extremely irritant), benzene (carcinogenic). For a hobbie lab, it's not safe, i think
This is better made via Grignard reaction with benzyl chloride and acetonitrile . Smells sweet too.
Can i use Formaldehyde instead of acetone??
Formaldehyde is an aldehyde, not a ketone, and any other ketone can be used instead of acetone
FO^- can't exist to my knowledge because of the electronegativity of fluorine being higher as the electronegativity of oxygen - so you should be correct
Is it possible you are adding too much acetone? Unless your jugs are not regular 3.6 litre ones and your concentration is different than 6%, then it seems so. For every 3.6 litre jug you should add 75 ml of acetone if it is 6% bleach. That is what I calculated anyways. I would do 70 because acetone and chloroform cause an azeotrope and then your chloroform would be contaminated with acetone, which would be very hard to remove, so a little less is good. I could be wrong, because your percentage is probably higher than 6%, may be 10? Just curious, I am sure you know what you are doing. Its actually just for my info if I calculated correctly lol. Great video - keep them coming.
I notice in the video when he moves by one of the jugs it does say 10%.
As Doug mentioned the reaction is finished if the green color of the chlorine swaps to colorless.
Too much aceton is problematic because aceton boils earlier (56 celsius) than chloroform (61 celsius).
Aceton dissolves in Water so it is not cost efficient to destill it out. Be carefull !
CH3COCH3 + 6ClO- ---> 2CHCl3 + CO2
Awesome video 😊
Why cant you distill the rest of the water containing the 60 ml soluable chloroform?
Probably because it may behave like an azeotrope 🤔
But what about phosgene?!
can anyone help me appreciate it already: the doubts are to boil the sanitary water would increase the concentration of sodium hypochlorite? or you can also use the pool of sodium hypochlorite? and move these measures 1/50 to half and half what happens ???
What?
Boiling destroys NaClO.
Forming NaClO3 +NaCl
Will chloroform dissolve the plastic jug if left too long
no, it'll form phosgene and hydrogen chloride when exposed to oxygen over a long period of time
Can I use calcium hypochlorite instead of sodium hypochlorite?
I don't see why not . In solution the sodium and hypohalite are disassociated ions
Most calcium hypochlorite (in my experience) has insoluble crap mixed in.
I tried it with 1 liter bleach bottle and 15 ml acetone, didn't cool in freezer but did the reaction in ice bath, left it over night (I sealed the bottle so it was under pressure when I opened it) and ... nothing. No chloroform layer at all. Can somebody explain what I did wrong?
***** Thank you!
Also the amounts have to be very close to exact, or have an excess of bleach as Chloroform forms an azeotrope with the acetone.
adding brine, would the yield be higher?
16:20 my bad
No
actually, NaFO does exist
So how can I buy some from you I need sleep at night
Bad idea. It is carcinogenic. That is why they stopped using it for an anesthesia. Better to work to the point of exhaustion. Then no problem going to sleep.
I did his once on a smaller wc ale and everything just went brown, great for unblocking the drain though
I hope you don't have PVC pipes or it could easily "unblock" the drain sideways into your house.
There was still some chloroform in the cloudy supernatant. You should have given it more time to settle.
Love the vids man. Wanted to ask: I watched your vid on the dean stark apparatus and it got me wondering whether you couldn't use that to separate the water from the chloroform?
Am kinda on the fence about it, because increased temp. typically means increased solubility (so the hot mixture may just end up dissolving more chloroform into the water, even in the trap), but then again, I'm no expert on all this, which is why I watch these videos. Feel like they fill in the gaps from all the main 'takeaways' I ended up missing in my chemistry education... lol
Could one distill all the liquid from the jugs to get a better yield?
Nice vapor line. Liked just for that.. lol
very interesting thanks love your channel and your zhmapper one 2
Use Ca(OCl)2 not NaOCl to make Chloroform
Michael Chauncey does it work???!!
Michael Chauncey I agree. I've used calcium hypochlorite and it uses up a lot less space. It just requires a lot more care because everything is a lot more concentrated and it runs away a lot easier. Ice cold efficient condenser is a must.
Thanks for the tip!
Many process ...to make in cholroform..
@Kineg Salomo it is Ca(ClO)2
wtf dude your fucking awsome how the hell do you have 805 subs well make that 806 i just subscribed
Try steam distilling the waste aqueous phase. The CHCl3 is more volatile, so it should all come over before much water is distilled over.
A three neck distilling flask should be used to speed the process.
Rig one arm to siphon off the spent aqueous phase. Use an addition funnel to input more waste aqueous phase.
Save overhead aqueous phase for recovery by re-distilling.
Report results/yield in future TH-cam video.
Dead channel?
You poison yourself? Where you disappear to?
Can you make a video on how to make LSD
There are others now, but I think you can compete with them in videos like this.
Pool shock easier
That thumbnail is clickbait for chemists. The flask should not be that full! I must click to see why it is! :D
Me too, I couldn't belive he made so much chloroform
you've gotta question a guy who makes a metric shit ton of chloroform.
You can't actually kidnap anybody with a rag wet with chloroform, it takes minutes to make your victim pass out.
+Codex Necro
Do you know from experience?
basic common lab knawledge. if chloroform was the movie-stuff we wouldn't use it in labs, too dangerous. Looking into anesthesia from ye olden days, they used to soak a handkerchief in chloroform and drape it over the patients face for about 20 minutes. then hope that the patient wasn't anesthetized to death. havnt found how they brought them back, but i suspect fresh air and or ammonia gas like with hartshorn.
+TheZabbiemaster
There are a few old documentaries on TH-cam about this topic if you are interested. I was just joking about the whole experience thing.
thatIlluminati _ Yea, I was trying to help stop the "omg chloroform halp" epedemic. thanks ill look the documentaries up. they might help me later ;D
What is chloroform used for? It look like a good project
Mostly as a solvent...earlier it was used as an anesthetic, but it increases chances of cancer, so it was replaced
it can also be used as an reagent (e.g. Reimer-Tiemann reaction, an ortho-formylation)