Making Chloroform
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- čas přidán 31. 01. 2024
- Welcome to Episode 6 of Molecular Playground! I perform haloform reaction by creating chloroform from two common substances: acetone and pool chlorinating liquid. It's not just an experiment; it's a journey into the heart of organic chemistry!
Mixing acetone with sodium hypochlorite initiates a chemical reaction known as the haloform reaction which leads to the formation of chloroform. This reaction isn't just about combining ingredients; it's a perfect example of how halogenation works in organic compounds!
Warning:
Chloroform is extremely pungent and a powerful solvent! Handle with gloves and plenty of ventilation!
To see more amazing content, check out Molecular Playground down here:
/ @molecularplayground - Věda a technologie
As someone with 5 years in the chemical industry and a masters in chemistry, this video is like an actual fever dream. I cannot describe how wild what you're doing is. I especially love how you're spilling it over the sides of the mixing bowl as if you''re making a cake
Thank you very much! It was completely unintentional as I was contending with very strong winds. The chloroform would have settled to the bottom so the little bit of aqueous solution that spilled negligibly affects the final product.
Lol fair enough. This video just came up on my feed and I was like oh cool a lab synthesis don't mind watching that. And then I was just like: Oh my god hes doing it in a kitchen bowl. Keep it up tho mate all good fun and educational, although it does seem like the video has a strange target audience.
For example: Being careful when using plastics and acetone, great advice for an aspiring chemist. But I don't know how many of them are making chloroform in their back yard, maybe you could include some reaction mechanisms or some stoich or something? Other than that great video mate
@@MolecularPlayground
@@yuiopqwerty2542chloroform synthesis is a pretty common project for amateur chemists, most use this method. I use calcium hypochlorite and sodium carbonate to make a really strong sodium hypochlorite solution in a 2l flask with two condensers and an addition funnel. That way is considerably more efficient, but it can run away if you aren’t careful.
lol, He should change his name to "Quick and Dirty Chemistry". His style is growing on me though.
@@WaffleStaffelhaha😂
You should add a little ethanol to prevent phosgene.
This channel is art. Keep up the sketchy fever dream chemistry in the park
make a sepratory funnel from a coke bottle ffs
I just love the chaotic energy :)
The solution becomes opaque mostly because there are tiny droplets of chloroform coming out of solution. Very cool video
I mean, and here I thought Cody's Lab was the _sine qua non_ of ghetto chemistry, but jeez...
Used to be chemplayer. That was such a great channel for dirty kitchen chem.
Nice. Never even thought about salting it out. I have just let it sit for a few hours and got a few extra ml to coalesce out.
You don’t want the solution to cool so much though because chloroform demonstrates inverse solubility-meaning it is less soluble in warm water than cool water
@@MolecularPlayground I was not aware of that, thanks. I start with the bleach bottle from the freezer, and the bottle reaches room temp shortly after addition of the acetone.
What I mean is that you should start it extremely cold to limit evaporation of acetone and chloroform as the reaction heats up. However, you should not let it sit for a few hours hoping more chloroform will be made because the reaction proceeds fairly quickly and letting it cool after reaction will increase the solubility of chloroform in water.
@@MolecularPlayground Yeah, I meant I was able to get a few more ml out of the waste after initial separation, accumulated as beads on the bottom. Does it decompose over time as well as change solubility?
If the solution is kept warm and sealed and you extract hours later, you should be fine and maybe even get more chloroform by that. However, overexposure can cost chloroform (albeit negligibly) by evaporation and oxidation to phosgene.
1:06. Ingredients- How about the acetone?
I subscribed cool content!
This guy made chloroform right under the sunlight 💀
I see your concern, but fear not! The thick aqueous layer would protect it from UV rays. When the chloroform is exposed (for two minutes to get it on film), conversion to phosgene is extremely slow. If it was fast, wouldn’t more people synthesize phosgene this way?
Its much easier to do the reaction in the original pool chlorinating liquid bottle instead of that bowl, it looks messy.
Also do the acetone addition in 2 steps and cool the bottle in the freezer between the additions.
I find that yield is moderately impacted if done in the bottle because chloroform can react with the plastic since it is a powerful solvent. Also, the reactants were chilled prior to mixing. If not, the solution would get very hot and evaporate most of the acetone and chloroform. Not to mention the reaction happens very fast and chilling between additions would be impractical.
Cool vid
Tips to make your life easier - do it all in the bleach jug.
You can shake the crap out of it with the cap on and decant once cool ;)
Salting out is an awesome tip, appreciating as i didn't think of it myself.
One time i needed a lot of chloroform and it was on a weekend... no suppliers were open.
10 jugs of bleach later... lol
Invest in a separatory funnel - best 30 bucks you will spend and your decantation nightmare will be over
Cheers!!
Thanks!
When I do it in a jug (with same concentration), I get anywhere between 60-80mL which is lower than the 100mL or so I get in a glass bowl.
Also, how much chloroform did you get out of those 10 jugs and what did you use them for? I regularly use mine to extract natural products like rosemarinic acid and eugenol.
Lastly, don’t forget to subscribe!
@@MolecularPlayground i remember the yields were around 80ml, but I'm sure some of them varied due to concentration variances in the hypochlorite.. i didn't think of using glass as the cost was pretty low and i needed it quick.
Same for me, my plants were starting to wilt and i wanted the aromatics before they degraded
If i were a well funded home lab, I'd use a jacketed reaction flask and keep the temp low to see if it affected yields... but honestly, it's not that hard to get where i am.
Did you have much issue with phosgene?
No. It’s much harder to make phosgene than ,anny expect (though I’m sure putting concentrated H2O2 in it will make it a lot). If phosgene could easily be made by letting chloroform sit out or even just heating it in air, more people would make phosgene this way.
Is that an old peroxide bottle? Does that plastic hold up to that? You know peroxide bottles are designed to vent right?
It is an old peroxide bottle. I am pretty sure it holds up, but I keep it in the freezer just in case it acts weird at room temp.
@@MolecularPlayground you did know peroxide bottles are designed to vent , and will with the high vapor pressure, yes? It's a safety feature so they don't pop on hot days, just leak a little. Also prevents failure in a case of rapid decomposition. The O2 just vents. Not secure enough to hold chloroform. If you got it in the freezer it won't evaporate as fast ,
... but an old solvent container works a lot better.
Surprised the plastic held up, that's cool to know.
What's a good way to judge the ratio of acetone to bleach? Assuming you haven't titrated the bleach and concentration is not what it says on the label?
For 10%, 31mL of bleach to 1mL of acetone. For 7.5% or 12.5%, you would multiply 31mL by 1.25 or 0.75 respectively. I found this by the following:
The molar mass of sodium hypochlorite is 74.44g/mol. Three moles are required to make a mole of chloroform, totaling 223.32g of NaOCl. Since it is a 10% solution (meaning 10g in 100mL), I divide 223.32g by 0.10 which gives me 2233.2mL. The molar volume of acetone is calculated by molar mass divided by density, being 58.08 / 0.7845 which is 74mL. You divide 2233.2 by 74 and you get ~30.2, but to err on the safe side I round to 31mL of bleach so I have a slight excess.
(Deep breath) I hope that made sense! And now that you understand the perfect ratio, you can manipulate whenever you use a different concentration of bleach like 4.5%, 7.5%, or 12.5%. If you need help with those conversions, I’ll be more than happy to explain!
@@MolecularPlayground OMG, you didn't have to do ALL the math for me, but thanks 😁.
That wasn't what I was asking though,
My wife watered down the bleach without telling me, and I just ended up with a gross excess of acetone so I couldn't drop out whatever chloroform was made because it's more soluble with all the acetone.
So, what I was asking, how could I tell if things were going wrong before I wasted all the bleach and acetone, or even better what's a good way to titrate the bleach as it's never what it says on the label.
Often there is some detergent too, even if it says otherwise, how to handle that?
I heard there's a way using pool shock, calcium hypochlorite, any tips?
I’m sure your solution went completely clear (not even a hint of green). That’s a good indicator of using too much acetone. To titrate, it would be hard to explain procedure but basically you add hydrogen peroxide or hydrochloric acid and have the oxygen or chlorine gas be pumped into an upside-graduated cylinder with water in it. The gas will displace a certain amount, and you will find your concentration. I suggest you watch the beginning of Nile Red’s chloroform as he shows how to titrate bleach. Don’t use pool tablets (made of trichlor, not hypochlorite) but you can use calcium hypo to strengthen your solution. Do at your own risk though as higher concentrations increase risk of evaporation.
@@MolecularPlayground Thanks! That's very helpful!
Sounds like the basic rule of thumb is , if too clear add more hypochlorite.
But in the interest of being less sloppy, regarding titration, is moles of gas to moles of bleach 1:1 or 2:1? If you know off hand... I don't have the formulas memorized... I'll look them up eventually if you don't respond...
A “mole of gas” has way different physics to a “mole of bleach.” A mole of gas has a (near) perfect volume of 22.4L. If you titrate 10mL bleach with 10% hydrogen peroxide and generate let’s say 22.4mL of oxygen gas, 22.4mL divided by 22400mL is 0.001mol. 0.001mol divided by 0.01L of bleach is 0.1M NaOCl which is roughly 7.4g NaOCl per liter of bleach, or 0.74% NaOCl (g/100mL). Hope that helps!
ah yes the decanting bucket
my brother in christ use two bowls
You might think the spillage was caused reckless stirring, but it was a very windy day. Getting the plastic wrap on to seal took about five minutes no joke!
Smell it, you won’t 😂
Unfortunately not filmed, but I did smell it. It has a pungent minty odor. Don’t forget to subscribe!
It’s really not that potent. Takes like 5 minutes of direct inhalation to knock you out.
just do it in the jug , add acetone [ both chilled, shake well ] and back in the freezer over night and voila' , done loosely put the lid on for burping
You will lose some chloroform that way. When I did it a few times in the jug for preliminary tests, I lost anywhere between 10-30mL of chloroform.
Why?
I need a solvent that can extract anything from everything. It is much more efficient and less harsh at extracting natural compounds than steam distillation. It’s not a cure for insomnia I swear. Hope that helps and don’t forget to Subscribe!
Liquid bubbles are called droplets
Thanks lol!
Oh god...
Alright kids, please be sure to do this IN SUNLIGHT to ensure the highest quantity of phosgene possible.
I wish phosgene formed that fast! It could be a real viable route to making easy phosgene over trying to combine fickle, poisonous, and invisible carbon monoxide gas with odorous chlorine gas.
But for real though, the initial aqueous layer protects it from oxygen and harmful UV rays. After decantation, I show off yield and quickly dry it with magnesium sulfate before sealing in a dark bottle. If phosgene formed that easily, wouldn’t more chemist be making it from chloroform than the aforementioned way?
Make bromoform
i fw you heavy
To get out what's at the bottom of the bowl, use a syringe 👍
Chloroform is a powerful solvent that will muck up the rubber stopper inside the syringe. The acetone alone started doing a bit of damage and makes it harder to push.
@@MolecularPlayground Glass syringe could work.
Bro this yield is very poor i think
The molar volume of acetone is 74mL. I used 125mL which is 1.6mol. The molar volume of chloroform is 80mL. The volume of chloroform I extracted is ~100mL which is roughly 1.2mol. That’s roughly a 75% yield. It may not seem like a lot because I used a big gallon of bleach that only “excreted” that little bit of chloroform, but it is because of the sodium hypochlorite content. Imagine how much lower the yield with plain bleach!
I don't mean to dogpile, but pool bleach usually has a max concentration of around 12% by weight, which means 88% of that bottle is water. There are also a couple minor side reactions but those are minor. The yield here is about standard.
But, just in case you think can increase the efficiency by using higher concentrations of hypochlorite bleach, or pool tabs...DONT! You need that volume of water act as a heat sink to prevent runaway boiling, that can boil off the acetone, the chloroform, and create gaseous side products.
Don’t be so modest. You are completely right! I used a near freezing gallon of pool bleach and acetone that spent the night in the freezer, and the reaction heated up to 100-110F (estimated by touching, it was not scalding or even uncomfortably hot). That’s still enough to make acetone and chloroform volatile and more easily evaporate. I can’t imagine using a a higher concentration that won’t impact yield by overheating.
Thanks 😊
I've just siphoned out the chcl3 w the large syringe you have.. personally I like baby nasal suckered for siphoning, but that's me. ❤
When will I find a date I'm lonely.
You can't find a date and watching a chloroform video?