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stygian
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oh silver nitrATE.. I see now.
Regardless, at a quick glance the formula that somebody else posted looked like trinitromethane, which I was merely commenting upon. Not even my idea
in the first place thank you.
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woelen
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Silver nitrITE (not nitrATE) can be used to make nitroform. I'm not sure whether this can be done from chloroform. The description I have seen starts
from iodoform, making AgI and CH(NO2)3.
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Slimz
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would pool shock wich is not Sodium Hypochlorite react with acetone?
edit i think its
dichloroisocyanurates wich is a clorine donor.
[Edited on 28-9-2007 by Slimz]
Johnny was a chemist’s son, but now he is no more. What Johnny thought was H2O was H2SO4
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guy
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Yes it would but you need to add enough sodium hydroxide to generate hypochlorite and to deprotonate the acetone
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Slimz
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anyone have any suggestions as to ammounts. the dichloroisocyanurates is powdered (99%-100%)
the lye will also be powdered (red devil brand or something similar)
And would this method have a higher yield?
[Edited on 28-9-2007 by Slimz]
Johnny was a chemist’s son, but now he is no more. What Johnny thought was H2O was H2SO4
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woelen
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Don't mix the pure dichloroisocyanurate powder with pure acetone. That almost certainly will result in a very violent reaction, possibly with fire.
There is a thread on this subject already, Garage chemist has done a lof of interesting experiments with making chloroform from TCCA & Co.
http://www.sciencemadness.org/talk/viewthread.php?tid=5686&a...
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Slimz
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thnx.. ill read it...
Johnny was a chemist’s son, but now he is no more. What Johnny thought was H2O was H2SO4
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Phosphor-ing
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Wasn't this thread a sticky a few days ago?
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Slimz
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no i think it was just very active..
Johnny was a chemist’s son, but now he is no more. What Johnny thought was H2O was H2SO4
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Aqua_Fortis_100%
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Thats my last week of holidays, so I did some shots for this old project. I would want DCM because is less toxic than chloroform and usually have same
dissolving properties. But because not only chloroform but also methylene chloride are watched here (hence I dont know any OTC product here for both
susbstances), I think chloroform synthesis would be easier performed on homelab than DCM.
In the backyard some ~120g of (old) poolshock 65% calcium hypochlorite was measured out and added to a large glass container (about 3 L) then 900mL of
water (+ 5g NaOH) added to it.
(I was fearing chloroacetone formation, so I added NaOH, but only after experiment and more careful reading I payed attention to the fact that NaOH
isnt really necessary since the reaction produces its own base. )
12 ice pieces (each made with about 50mL of water) were then added.
~45mL of acetone ( distilled from a nail polish remover) were mixed with ~150mL of water and this solution was then slowly added to hypo/ice
suspension with stirring.
After some minutes from the last addition the smell its totally different. Quite a 'sweet' smell, like all people says.
This mix was left overnight in hope to give better yield.
In the next day the mix was heated in a homemade distiller. In the receiving flask was put some ~30mL water to avoid evaporation of colected
chloroform and the flask was put on a ice/water bath for same purpose.
In the start of the step, the tube of distiller started to bubble a unknow gas through the water of the receiving flask. And this gas bubbled through
all the distillation. Dont think that would be any chloroacetone though. The white suspension on distilling flask formed a froth and in the end
nothing was collected. 
I repeated the experiment today, but using less water and also did the modification proposed by polverone: using a greater excess of acetone (all hypo
consumed) and neutralizing the calcium hydroxides in the end with HCl.
~120g of hypo was added in a water/ice mix (~300mL water + ~650g ice(13 pieces)) and stirred. Slowly and with vigorous stirring, ~60mL of acetone was
added (addition finished in about 5 minutes, without the mix getting warm to touch and ice already floating on it).
This mix was agitated more time and left to stand about 4 hours.
Then, with stirring, it was slowly neutralized by concentrated HCl. Some bubbles were visible and then I put my face backwards and continues mixing.
After all was dissolved I could see a large blob of chloroform (~5mL) on the bottom. I extracted the raw chloroform with a dropper and measured:
~6,5mL in a small graduated cilinder.
The solution containg chloroform was then distilled in the backyard with the same setup used before. A slight chocking gas started to evolve but drops
of a liquid started to distill and in the end I collected about 8mL of a yellow/green imiscible liquid a the bottom, maybe contaminated chloroform.
I extracted it and breathed (not deep though). In the start it smells like chloroform but after it burns a lot! My eyes started to tear somewhat...
argh.... If this is chloroform contaminated with chloroacetone (but probably could be) or other substances I dont know, but I think it wont be easily
purified by further distillation, so I added it to the solution from which comes and I soon will destroy all with feonton's reagent before throw all
of it away.
The only word I can use here (but thinking in worse words) for that wasted time is PITA!!!! 
Now, the natural question would be: how could I get higher yields of calcium hypochlorite method without distilling the calcium suspension?
I was thinking in make conc. bleach from Na2CO3 and Ca(OCl)2, filtering, reacting with acetone, extracting and distilling.. But seems more work..
BTW, was BromicAcid the only person here that tried the electrochemical method?
[Edited on 23-2-2010 by Aqua_Fortis_100%]
"The secret of freedom lies in educating people, whereas the secret of tyranny is in keeping them ignorant."
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bbartlog
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I've only done this with 6% NaOCl solution, not calcium hypochlorite. The reaction seems to proceed fairly easily with NaOCl, so my first thought is
that the Ca(OCl)2 just doesn't work as well for some reason (maybe the limited solubility of Ca(OH)2 as opposed to NaOH).
Like you I've also found that trying to distill dissolved chloroform from the aqueous phase in an attempt to increase yield is just not worth it. You
won't get much more than you already have in the dense phase at the bottom, and there will be contaminants to deal with.
Couple of other comments on your second attempt, based on my own experience:
The liquid volume is still kind of large IMO given that you are using ice. You would want this much if you were just using RT water, but with the
ice you should be able to cut the liquid volume further. Just using straight room temperature bleach I end up with 830mmol per liter, and either use
no cooling (if I'm not mixing) or just dip the flask into cold water if I am mixing to speed the reaction. The temperature doesn't get above 70C which
suggests that we're only looking at about 60Kcal per mole (of bleach) of heat. With the Ca(OCl)2 we would assume twice that per mole. In your case you
have about 550mmol of bleach which should net no more than 60-70Kcal of heat(*). If you start with 660g of water with 2/3 of it frozen and the rest at
0C (similar to your ratio, but with 1/3 less) then the temperature should not go above 50C. Further, it seems to me that if you set yourself up to
distill directly from your reaction vessel, the heat (up to a point) will work in your favor by driving the chloroform out of solution and into the
vapor phase, before any possible reaction with base could take place.
You could probably look up the actual heats of reaction if you wanted something better than my back-of-the-envelope figures.
I also don't think neutralizing with HCl is useful unless you can distill the aqueous phase successfully (and that doesn't seem worth it). In the
case you describe, there's already been four hours of mixing for possible degradation of your product to take place, so you clearly aren't saving the
blob of CCl3 by neutralizing at this point.
I have used an excess of acetone (and also an excess of bleach) and not seen any noticeable improvement in yield over using exact stoichiometric
ratios. Using excess acetone tends to result in the formation of base-catalyzed condensation of the acetone, though this does take longer than the
haloform reaction we want. In your case, I'd wonder about the rate at which different chlorination reactions take place. If the first chlorination (to
chloroacetone) and the second (to dichloroacetone) proceed at speeds close to the third (from dichloroacetone to trichloroacetone), then an excess of
acetone means you'll produce appreciable amounts of mono- and di- chloroacetone that don't get fully chlorinated before the hypochlorite is exhausted.
Though I don't know anything about the reaction kinetics it wouldn't surprise me if this partly explains your low yield.
Finally, when starting at room temperature (and then rapidly rising to 60C+) this reaction takes only a few minutes to complete. Maybe with
everything kept around 0C it takes four hours or more but absent some nice improvement in yield I don't see much reason in keeping it cold.
My suggestion would be to try the reaction using 12g of your hypochlorite and 100ml of cold water (but no ice), with a stoichiometric amount of
acetone (if your hypochlorite is 65% Ca(OCl)2 then this would be 2.1g). If the heat seems manageable (or not) you can then adjust the amount water and
scale up.
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Aqua_Fortis_100%
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Thank you very much by comment bbartlog. I will keep this info on mind if trying it again..
Im inclined to use Ca(OCl)2 method since household bleach here sucks (the concentration in "active chlorine" is only about 2-2,5% and if I did right
math, this means a almost similar hypochlorite concentration, that is much lower than yours 5-6% NaOCl) and 12% variety is very hard to come (and also
is quite expensive).
Using 500mL of this crappy bleach I obtained in the bottom only a small blob (0,5mL, at best).
Yesterday I did a second experiment, making a somewhat more concentrated bleach from Ca(OCl)2, based on a experiment from garage chemist according to
this thread: http://www.sciencemadness.org/talk/viewthread.php?tid=8504#p...
(Ive did this before, but at much lower amounts, for hydrazine sulfate and semicarbazide chloride synthesis)
I did a slurry of ~250g of Ca(OCl)2 65% + 750mL water + 150g ice then a cooled Na2CO3 solution (made by boiling ~500mL water and mixing with ~190g of
dehydrated Na2CO3) was added to it. The CaCO3 precipitation was immediate and quite a while after adding all of the solution, the suspension turned
very viscous and very hard to stirr.. I stirred for 5 mins with a big plastic spoon and the suspension turned again liquid.. I left it for about 30
mins and then filtered using first a piece of cloth then filtering again through filter paper (2 or 3, because if using one at time the strong
alcaline bleach is likely to perfure it). This is the messy and very boring step as filtration is very slow.
In the end I obtained ~1100mL of a pale green liquid that I chilled in the freezer (and also added some ice to speed up.. about 300g) and then added
slowly and with stirring 70mL of non-distilled nail polish remover. After some minutes along with good smell, appeared also some white, flocculating
precipitate that quickly settled. I left it overnight and then today I see a large blob of chloroform on the bottom, carrying some of the precipitate
with it..
I will try to distill all of it tomorrow (Unfortunatelly I cant do this today.. I hope that I dont lost much chloroform).
| Quote: | | Further, it seems to me that if you set yourself up to distill directly from your reaction vessel, the heat (up to a point) will work in your favor by
driving the chloroform out of solution and into the vapor phase, before any possible reaction with base could take place. |
After my crude experiments and more detailed experiments from other people, that seems to most promising when working with hypochlorite, although
there will be some problems (froth, foaming, some chloroform reacting, etc..)...
The guy from the videos below obtained some very large amounts of chloroform using calcium hypochlorite... I wish to have similair professional
distilling setup one day, at least on my dreams 
http://www.youtube.com/watch?v=IdfHMz7WeXI&NR=1
http://www.youtube.com/watch?v=Wh_7fjHV_BY
So, by above videos and from reports from other people in this thread, calcium hypochlorite is much more interesting as OCl- source than dilute sodium
hypochlorite, but in real life it seems that when not controlling parameters such as water content, temperature, etc and even more when using
improvised equipment (like I) will NOT be too easy to reach any good yields.
Arghhh
Water, a necessary evil...
"The secret of freedom lies in educating people, whereas the secret of tyranny is in keeping them ignorant."
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entropy51
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Chloroform
50 gm Ca(OCl)2 and 150 mL H2O was placed in a 1 Liter RBF equipped with magnetic stirring and a reflux condenser and surrounded by a cold (not ice)
water bath. 19 mL of acetone was added cautiously, first in 1 mL portions through the condenser until the mixture thickened and foamed. Add remainer
of acetone in small portions to maintain a gentle reflux without heating. Finally stir for one hour and arrange condenser for downward distillation.
Distill off the CHCl3 using a hot water bath. BP = 60 - 63 C. Yield was about 15 mL.
It is important to use an oversize flask as the reaction foams vigorously.
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Rich_Insane
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Hey everyone, I did an experiment. So here's what I did. I calculated that for 10 ml of Acetone, I would have 0.135 mol of it.
Now the reaction is Acetone + 3NaOCl --> CHCl3 + 3H2O, so I needed three times as much NaOCl. That's 0.409 mol, which is 30.44 g. The bleach I have
is 6%, so i figured that I needed 507 ml of that bleach with 10 ml Acetone to yield 10.94 ml of CHCl3 (theoretical yield).
So I measured out 250 ml of bleach and put it into a 400 ml beaker. The reason I didn't add all of it was because the beaker was only 400 ml capacity,
so I would have to get rid of some of the aqueous layer first. Then, in a cooking pot, I added a lot of ice and water and stuck the beaker in with a
thermometer. I then added a very small amount of acetone and watched the bleach go from yellow, to cloudy. I stirred gently with the thermometer.
http://img379.imageshack.us/img379/6924/1002256.jpg
After that, I slowly added 100 more ml and a tad more acetone. I stirred and watched the temperature, not letting it go a degree above 30 Celsius.
I measured out the rest of the bleach and added the rest of the acetone, slowly pouring out excess aqueous junk. Then, after about 10 minutes, I took
the beaker out, and using a disposable pipette, sucked out all the chloroform I could get. I put this chloroform into a small beaker, and for purposes
of showing to all of you, put it in a test tube.
http://img638.imageshack.us/img638/7507/1002271.jpg
I took this and washed the impurities out by adding tap water, then pipetting as much water as possible out. In the process I lost probably 0.1 ml of
CHCl3. The final product was measured in a 10 ml graduated cylinder shown below.
http://img62.imageshack.us/img62/4595/1002276u.jpg
My yield was around 5 ml, which is 45.67% of the theoretical yield. I dropped 1 ml on the ground and watched it evaporate quickly like chloroform.
Then I transferred to a vial.
http://img709.imageshack.us/img709/5945/1002278a.jpg
I decided to keep this CHCl3, so I added some diluted acetone onto the layer, sealed in a plastic bag and put it in the freezer.
http://img641.imageshack.us/img641/3605/1002285.jpg
The two reagents I used were:
http://img714.imageshack.us/img714/1047/1002259.jpg
and
http://img175.imageshack.us/img175/339/1002257.jpg
 Pictures are way too big. Could someone tell me how I can resize them on
Imageshack?
[Edited on 14-3-2010 by Rich_Insane]
[Edited on 17-1-2011 by madscientist]
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Formatik
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Quote: Originally posted by entropy51  | Chloroform
50 gm Ca(OCl)2 and 150 mL H2O was placed in a 1 Liter RBF equipped with magnetic stirring and a reflux condenser and surrounded by a cold (not ice)
water bath. 19 mL of acetone was added cautiously, first in 1 mL portions through the condenser until the mixture thickened and foamed. Add remainer
of acetone in small portions to maintain a gentle reflux without heating. Finally stir for one hour and arrange condenser for downward distillation.
Distill off the CHCl3 using a hot water bath. BP = 60 - 63 C. Yield was about 15 mL.
It is important to use an oversize flask as the reaction foams vigorously. |
Higher yield was described by Orndorff and Jessel in the American Chemical Journal, using a synthesis employing 275g Ca(OCl)2 with 33.3%
active Cl in 800ccm water and 22g acetone in 70ccm water, yielding 36-38g CHCl3.
Attachment: Orndorff, Jessel, Am. 10, 365.pdf (337kB)
This file has been downloaded 845 times
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Eclectic
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(BUMP)
Did anyone ever figure out what the White precipitate is? I tried this with 3 gallons Clorox Outdoors in a 5 gallon plastic bucket,
assuming it was 10% sodium hypochlorite, with 350 ml acetone. Clorox was set in chest freezer @ 0.0 F for a week and was found
to be same consistancy after stirring with paint stirrer on drill as a "Slushy" frozen beverage. Acetone poured in over 30-60 seconds
with vigorous drill stirring. No problems. Ice took about 20 minutes to thaw, And temp never got above room temp (outside, 45 F).
[Edited on 1-16-2011 by Eclectic]
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bbartlog
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Which white precipitate where? I skimmed a couple pages of the thread but am not inclined to reread the entire thing to figure out what you're talking
about.
| Quote: | I tried this with 3 gallons Clorox Outdoors in a 5 gallon plastic bucket,
assuming it was 10% sodium hypochlorite, with 350 ml acetone. |
Doesn't the bottle tell you what the percentage is? In my neck of the woods my default assumption would be 6%, but on the plus side I don't need to
assume because all of the OTC bleach actually tells you what % strength it is. Don't know why the ammonia isn't labeled the same way.
Also beware of some of the outdoor bleach-type cleaners, they have other stuff in them besides hypochlorite and hydroxide.
So how was your yield after the above? How did you get the chloroform out? Also I'm surprised that your temperature didn't rise a little more; with
10% bleach I would expect a rise of maybe 60-70C, but I guess that if there was a lot of frozen slush in your mix then much of the energy went to melt
the ice.
In a related vein, I recently performed the haloform reaction using methyl ethyl ketone (2-butanone) rather than acetone. I mixed 3630g of 6.15%
sodium hypochlorite solution with 72g of MEK in a one gallon pickle jar, with both reagents starting at -5C temperature due to the frosty conditions
out in my barn. Stirred intermittently. Reaction took a while to proceed, but after about 40 minutes the temperature had risen to 45C (which was where
it topped out). Unfortunately I then had to let this stand for a couple of days before getting back to it, which may have resulted in some hydrolysis
of the chloroform at the bottom. After decanting most of the top aqueous phase I separated the remainder in a separatory funnel, with a net of 45g of
chloroform. Only 38% yield and that's for crude product, I imagine it will drop more once I've redistilled it.
Anyway, besides comparing yields on this (MEK versus acetone) I wanted to see whether this was at all viable as an OTC route to propionic acid; I will
see if I can work up the aqueous phase and get any propionic acid from it.
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Eclectic
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Freezing the bleach to a slush to avoid needing ice was the main point of
the experiment. It seems to work, and allows rapid addition of the
entire amount of acetone with vigorous stirring. I'll do some workup
today. I could not find a hypochlorite % on the label, but MSDS for both
"Outdoors" and "Deck Cleaner" say 6-10%.
I got about 1/2 gallon heavy emulsion and floculant white precipitate.
Distillation would be only practical way to do workup. There does seem
to be some kinda detergent in the "Clorox Outdoor". Lots of soapy bubbles cleaning up bucket.
[Edited on 1-16-2011 by Eclectic]
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The WiZard is In
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TCE was used at one time as an anesthetic in child birth! And
widely in industry to clean electronic components.
Not that many years ago you could but it OTC, then it was
banned as a carcinogen. It had replaced OTC carbon tetrachloride
when that was determined to be carcinogenic. It was replace
by 1,1,1 trichloroethane. Which was ..... you got it!
At not extra charge ... for a short period acetylene was used
in Europe as an anesthetic.
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The WiZard is In
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Sorry I gave up reading this thread, I have never seen so much
chemical silliness and speculation.
Chloroform is easily made (worked for me many-many moons
ago) by reacting calcium hypochlorite and acetone. If you are
planning on living forever just mix them, or to speed things up
boil them together, actually it take some time — reflux.
2CH3COCH + 6CaOCl2-H2O = 2CHCl3 + 2(CH3COO)2Ca + 2Ca(OH2) + 3CaCl + 6H2O
Don't worry 'bout stocio. just be sure to use enough hypochlorite
to react all the acetone. You can distill the chloroform off if you want.
Noted in passing —
Linda Stratmann
Chloroform : The Quest for Oblivion
Sutton Publishing 2003
Byda it was originally made by it discoverer by distilling ethyl
alcohol with chloride of lime.
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bbartlog
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Mixing solid CaOCl2 and acetone is not such a good idea; the reaction is fairly exothermic. Not sure it would actually catch fire but it would sure
boil off the chloroform in a hurry, as well as unreacted acetone and other intermediate products.
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bbartlog
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| Quote: | | I got about 1/2 gallon heavy emulsion and floculant white precipitate. |
Weird result. But I think I see the problem: Chlorox says (on their site, see: http://www.thecloroxcompany.com/cgi-bin/form_ingredients.cgi... ) that the outdoor cleaner is not just hypochlorite. It has a bunch of crap in it
(the MSDS says: Water, Sodium hypochlorite, Sodium chloride, Cetyl betaine, Sodium carbonate, Sodium hydroxide, Sodium silicate, Sodium xylene
sulfonate).
Couldn't guess what your emulsion and precipitate are but I think you should do this reaction with plain bleach.
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Eclectic
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Yes, pure sodium hypochlorite solution is better. The emulsion is
chloroform and water, but it's never gonna break and separate because
of the detergents. But I did verify that freezing ice out of 10% sodium
hypochlorite at 0F will make additional ice unnecessary.
[Edited on 1-17-2011 by Eclectic]
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Eclectic
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Experiment was retried with 2X184oz bottles 6.15% Sodium Hypochlorite.
Poured in 5 gallon plastic bucket and frozen overnight in chest freezer.
Slush was stirred with drill operated paint stirrer and 1 cup acetone was poured in with vigorous stirring. A plastic lid was snapped on, and mixture
was left overnight, yielding 200ml crude water white CHCl3
after decanting top aqueous layer.
Both phases were transparent with no sign of precipitate or emulsion.
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trezza
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Hello all, Tonight I attempted a chloroform synthesis following this web page: http://www.erowid.org/archive/rhodium/chemistry/chloroform.h...
I scaled it down to 2/5ths because I don't have large glassware to use.
About half way through adding the acetone with a pipette the flask quickly filled up with a white frothy stiff mass and became fairly hot, it appears
to be calcium hydroxide as it is just barely soluble in water.
I used a granular pool salt claiming to have 700g/kg chlorine as calcium hypochlorite, nothing else is listed.
What has gone wrong here and why?
[Edited on 4-3-2011 by trezza]
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