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cyanureeves
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would i be able to make some iodoform with some tetraglycine hydroperiodine? it readily turns orange with just water. maybe if i dissolve in in water,
add the acetone then the sodium hydroxide solution. anything but phosgene! because i wouldnt mind making my own antiseptic. every time i go to my work
shed there are always sulfuric fumes of sorts or hydrochloric and it attaches to the sweat on my face and itches. also there is carbon dioxide for
sure from spills on wood etc..and gnats love that stuff. i've never had a good complexion but damn, bumps at fifty?people might stop shaking hands
with me.
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Sedit
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It sounds like water purification tablets. I handled them years ago the same way I handled Povidone iodine. Mix it with NaOH and heat it till your
left with nothing but ash which contains your NaI. Dissolve in water and filter. Proceed as you normally would with NaI solutions.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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cyanureeves
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well i heated the water purification tabs with sodium hydroxide then added water and got no iodine color. so i added a dash of acetone and h2o2, then
a about 100 ml of bleach and it all fizzed but no orange color. i did get to smell the cut grass odor though i did not take deep whipfs. i must say
it is very,very pleasant smelling though not watermelon-like as my cut lawn,but better than chloroform. i then added about 15ml of sulfuric acid and
instantly the whole thing turned orange and my shed smells like betadine now. i think i see a precipitate also.
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mewrox99
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Is this cut grass odor phosgene?
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ScienceSquirrel
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Mood: Dogs are pets but cats are little furry humans with four feet and self determination! 
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No
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mewrox99
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Speaking of phosgene. It's now been 80 hours since that whole scare I had. With zero symptoms I guess this is an appropriate song
http://www.youtube.com/watch?v=Y6ljFaKRTrI
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cyanureeves
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no not phosgene or i'd be dead but not chloroform either. i did smell chloroform at first of course with the acetone. this mixture is a chameleon
like solution, yesterday it was orange then it went white when i added more bleach, then it went back to orange as it sat in the sun.this morning in
my shed its white again. i think i'll just buy potassium iodide.yep youre still alive and soon you will be back rockin to highway to hell. such
ungratefulness!
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Jor
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Did you heat your iodoform directly with a flame or from beneath in container, and was it still wet? Most likely you did not even make phosgene !
[Edited on 25-5-2011 by Jor]
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Dr.Bob
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Quote: Originally posted by mewrox99  | I thnk you should make a difrent thread for that. So just to confirm 44 hours and nothing means im fine? I also forgot 2 mention that after heating it
with the blowtorch there was some mess on the pan. I cleaned it with a paper towel and burnt said paper strongly with the bt. I hope that doesnt
change anything. I have NO symptoms but still concerned. Should i get my lungs x-rayed?
[Edited on 24-5-2011 by mewrox99] |
1) We're chemists, not doctors, but
2) If you have no symptoms and are alive, then you will not likely suffer any ill effects. Without symptoms, most X-rays will not likely show
anything useful. Meaning that if you had symptoms, then they might be due to physical problems that show up on an xray. Any remaining long term
issues from chemical exposures are very hard to detect by X-rays.
But I know several chemists who have had many exposures to harsh chemicals and if they were fine after a couple of days, they were OK. Two of them
are still alive and well after 85+ years, so all chemicals can't be as bad as the media claims.
Bob
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PHILOU Zrealone
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| Quote: Originally posted by Dr.Bob |
1) We're chemists, not doctors, but
2) If you have no symptoms and are alive, then you will not likely suffer any ill effects. Without symptoms, most X-rays will not likely show
anything useful. Meaning that if you had symptoms, then they might be due to physical problems that show up on an xray. Any remaining long term
issues from chemical exposures are very hard to detect by X-rays.
Bob |
I think he suffers from the survivor paradox symptom
"Hey its 1 hour and I'm still alive!"
"Hey its 2 hours and I'm still alive!"
"Hey its 1 day and I'm still alive!"
"Hey its 2 days and I'm still alive!"
"Hey its 1 week and I'm still alive!"
"Hey its 2 week and I'm still alive!"
"Hey its 1 month and I'm still alive!"
"Hey its 2 monthes and I'm still alive!"
"Hey its 1 year and I'm still alive!"
"Hey its 2 years and I'm still alive!"
"Hey its 1 decade and I'm still alive!"
"Hey its 2 decades and I'm still alive!"
"Heeeyyy iiittttsss 1111 ccceeennttuuurrryyy aaannddd III''''mmmm sssstttiiiillll aaallliiivvvveeee!!!! (But I suffer from Parkinsonian disease...I
knew that iodophosgen had injured me in some way"
"Hey its 2 centuries and I'm still alive!"(But answering from the other side, everything is fine, I play with Adam and Grand-Grand-Pa and Mom)"
ROFL-LOL  
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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mr.crow
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When I was a kid I "accidently" lit a plastic cupholder on fire making a terrible smell. I was sure I was going to die in 2 days.
Why on earth did you heat it? Just keep it in a vial or flush it.
Double, double toil and trouble; Fire burn, and caldron bubble
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mewrox99
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I heated it because I thought that was a good way to dispose of it. If I dissolved it in propanone and flushed it down the sink it would have stank
out my lab which is in a fairly confined space (I usually work outside).
The Iodoform was slightly wet and heated strongly with a blow torch.
Anyway, this issue no longer concerns me.
I didn't smell hay so I doubt there was over 1ppm entering my nose and even so it was days ago. I was only worried in the 24-72hour bracket where the
symptoms of pulmonary odema can take a little while to manifest. The lungs can't survive that long filled with HCl.
On the topic of phosgene poisoning. I am very surprised I cannot find a single reference online other than hearsay (Just2DIY on yt and him being
offline) about his death. Death by phosgene is probably one of the most atypicial ways for a 16 year old to kill himself so I'm suprised it didn't
make any news. I've googled his irl name several times
I would have expected an article like this (Phones death)
http://translate.google.com/translate?hl=en&sl=sv&u=... fficial&prmd=ivns
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Mailinmypocket
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I made a very small quantity of Iodoform this evening following Woelens suggested steps.
1g KI dissolved in 5 ml of 10% HCL
added 7ml of 3% H2O2 (probably could have stopped after 5ml) the typical precipitate of iodine crystals formed, allowed these to settle 5 mins and
decanted. rinsed with water.
Added 8ml water followed by 8ml Acetone, and agitated test tube 1 minute.
Added NaOH dropwise (exact quantity not measured but solution used was 1M) until the solution turned bright yellow with quickly precipitating
iodoform.
Allowed to settle, decanted. rinsed with DI water and filtered
In the vial shown, is the final product, havent weighed it yet as it is not completely dry.
***I took step by step pictures of my synth however they are too large to attach to the message board will convert at some point although they are pretty typical images***
[Edited on 27-5-2011 by Mailinmypocket]
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woelen
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This indeed is the right color of the product. Next time you can decrese the amount of acetone. Instead of 8 ml it is OK to use 2 ml. But using more
does not harm, it just uses up more acetone than is necessary.
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Paddywhacker
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The OP's method, using hypochlorite and KI makes more efficient use of the KI. You get more iodoform for a given weight of KI.
Making iodoform from iodine, some of the iodine is lost as iodide.
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woelen
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Did you read the rest of the thread? Adding hypiochlorite directly to a mix with iodide and acetone does not only lead to formation of iodoform, but
chloroform (and maybe mixed iodo/chloro forms) as well is formed. This is highly undesirable.
I know that 50% of the iodine is converted to iodide, but you can easily oxidize this again with some H2O2 and acid and do the iodoform reaction
again. Even a third iteration can be done without increasing the volume of the liquid too much. With 2 iterations, 75% of the iodine is used, with 3
iterations, 87.5% of the iodine is used. You even can keep the iodoform in the liquid if you don't make the liquid too acidic for each iteration.
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Mailinmypocket
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Ok less acetone is even better, I'm planning on scaling up the reaction after work this evening to obtain a few grams worth for future experiments. I
didn't really calculate the shoichiometry on this one and to be honest, that's an area of mine that needs more practice. Nonetheless I will reduce the
acetone and try again now as For the efficient use of KI, if the peroxide used
oxidizes all of the elemental iodine out of solution, would there really be that much waste of KI? I haven't had a chance to view OP's method yet but
I'm assuming that the hypochlorite performs the same oxidation as the peroxide does? Perhaps I will do a side by side test later and see what the
differences look like!
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Mailinmypocket
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| Quote: Originally posted by woelen | Did you read the rest of the thread? Adding hypiochlorite directly to a mix with iodide and acetone does not only lead to formation of iodoform, but
chloroform (and maybe mixed iodo/chloro forms) as well is formed. This is highly undesirable.
I know that 50% of the iodine is converted to iodide, but you can easily oxidize this again with some H2O2 and acid and do the iodoform reaction
again. Even a third iteration can be done without increasing the volume of the liquid too much. With 2 iterations, 75% of the iodine is used, with 3
iterations, 87.5% of the iodine is used. You even can keep the iodoform in the liquid if you don't make the liquid too acidic for each iteration.
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Wow, you posted that at the exact instant as I posted my last reply, all questions answered, thanks Woelen lol!
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trb456
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Bringing up this iodoform thread again to ask about purification. I've been reviewing the haloform reaction and Woelen's preparation. Assuming we use acetone as the reactant/solvent, and NaOH as the source of OH-, and strip out/balance
all the stages of the mechanism, we get the following balanced equation:
3I2 + CH3COCH3 + NaOH -> CHI3 + CH3COO- + Na+ + 3I- + 3H+
My question is whether or not anything else can be recovered on the right hand side of the equation. Assuming we wash the CHI3 with water, we are
left with an aqueous solution of the remaining ions. Everything in sight is highly soluble. The least soluble combination would seem to be sodium
acetate, but that's the least interesting thing we could recover IMHO. Also, things may be more complicated than this, given that the haloform
mechanism has many stages (see the above link).
This looks like a dead end, but I thought I'd ask a more experienced group. Thanks!
trb456
EDIT: Looking up BPs, it may be possible to distill off the acetic acid and leave behind sodium iodide, but there may be more interactions here that
change the BPs in ways I do not know.
[Edited on 10-6-2011 by trb456]
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woelen
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@trb456: A few posts earlier I explained how most of the iodide in the remaining solution can be used for further haloform reaction. In a single step,
50% of the iodine is used, with two steps, 75%, with three steps 87.5% and so on. Three steps most likely is most economical, above that, the hassle
of acidifying, oxidizing and basefying becomes too much for the small amount of iodine used for making more iodoform.
------------------------------------------------------------------
I also received a few questions about the reaction of iodoform with chlorine gas. I have done a few experiments to check what happens with this
reaction. I found it sufficiently interesting to make a small (text-only) web page about this experiment:
http://woelen.homescience.net/science/chem/exps/exppatt.cgi?...
The second experiment describes what happens when chlorine gas is passed over iodoform. Based on the results of this experiment I'm almost 100% sure
that no CCl4 is formed, but only CHCl3 and possibly lower substitution products like CHCl2I and CHClI2.
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hkparker
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I can't believe I didn't read this thread before my iodoform experiments, but I hardly ever go in the organic section here as I usually don't know
whats going on. Maybe I should, and force myself to learn something
I tried the bleach method and was really happy with the amount of product I got compared to your method woelen. Didn't realized the chloroform
produced was a problem and making mixed halogen haloforms. Guess it was too good to be true, sorry if I ever doubted you woelen . I'll update my video...
What about the bleach method and bromoform, can we expect the same problems with iodoform? I don't see why not. And if so could I make bromoform by
adding sodium hydroxide to bromine and acetone in water?
Lastly, I might have gotten a small amount of iodoform on my skin (impure iodoform, made the bleach way). The rest of the day I felt a little dizzy.
an MSDS sheet said that it can be easily absorbed through the skin, is it possible that was the reason I was dizzy?
My YouTube Channel
"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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mewrox99
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I doubt it was from Iodoform on your skin. Iodoform was used as an antispetic applied to open wounds.
It was probably CH2ClI or some other compound like that. These compounds are likely to be very toxic and probably is able to be absorbed through skin
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woelen
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As I wrote before, adding bleach directly to a solution of acetone and an iodide (or bromide if you want bromoform) is not a good idea.
You can use bleach, but with the bleach you first must make iodine (or bromine) in somewhat acidic solution. To that you add the acetone and then add
sodium hydroxide. Never allow the presence of excess bleach or excess chlorine.
The stoichiometry of the reaction is as follows:
3I2 + CH3COCH3 + 4OH(-) -> CHI3 + CH3COO(-) + 3I(-) + 3H2O
In terms of chemicals it is as follows:
3I2 + CH3COCH3 + 4NaOH -> CHI3 + CH3COONa + 3NaI + 3H2O
You, however, should use excess acetone and excess hydroxide in your experiment. Most expensive is the iodine and you want all of that to be used up.
From this reaction equation you should be able to compute the amounts of chemicals, needed for making e.g. 1 gram of iodoform.
I do not do the computations here (I leave that as an exercise for you guys) but roughly speaking you can say the following:
For each gram of iodine take 1 ml of acetone (large excess) and half a gram of sodium hydroxide (large excess). Dissolve the iodine in the acetone and
then add 10 ml of water. Dissolve the sodium hydroxide in another 5 ml of water and add that to the solution. Almost 0.5 grams of iodoform
precipitates. This can be scaled up.
If you don't have iodine but potassium iodide:
Take 1.4 grams of potassium iodide. Add 10 ml of 10% HCl or 10% H2SO4 and dissolve all KI. Add excess amount of H2O2 (e.g. 10 ml of 3% H2O2), such
that all iodine precipitates and only a fairly light brown solution remains. Let iodine settle, decant the solution, add a lot of water, let iodine
settle again, decant the water, and then add 1 ml of acetone. Swirl and let as much as possible dissolve. No need to have all of it dissolved, the
iodine is somewhat flocculent and is not compact.
Add 10 ml of water and then add the 5 ml of NaOH-solution with 0.5 gram of NaOH. Just over 0.5 grams of CHI3 will precipitate. Again you can scale up.
If you don't have H2O2 use bleach as oxidizer instead, but assure that no excess is added. Excess bleach redissolves the iodine and will lead to
chloroform and mixed haloforms. For this reason the use of H2O2 is highly recommended. Excess H2O2 does not redissolve the iodine.
Keep in mind that only 50% of the iodine is used. After precipitation of the CHI3 you can collect the remaining iodine with acid and H2O2 and use that
to make more CHI3. See above in this thread.
Spread the CHI3 on a piece of filter paper to have almost all adhering water absorbed in the filter paper (coffee filter is perfectly suitable for
this, but do not use paper tissue or toilet paper). Scrape the solid from the filter and allow to dry outside (not inside, the material has a strong
hospital-like antiseptic smell).
CHI3 is easy to store and keep around and does not introduce any special risks in your home lab. Keep in a tightly closed little glass bottle in the
dark. It can be used for some interesting experiments, but I would not make more than 5 grams or so. With 5 grams you can do all interesting
experiments you might have in mind.
This reply should answer the U2U's I received recently about the making of CHI3.
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hkparker
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Thank you for your time woelen, I appreciate it. Me and mewrox99 both felt a dizzy and anesthesiated feeling on exposure to the impure iodoform. Do
you think this is likely from the CHI2Cl and CHICl2 impurities we produced?
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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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woelen
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I know that CHI3 itself does not induce a strong reaction, unless a lot of this is inhaled. In the past it was used as antiseptic and the people
treated with this almost certainly did not have such strong adverse effects.
So, I think that indeed the other mixed halogen compounds cause the dizziness.
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