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Author: Subject: Garage Experiments With Trichloromethane.
Haggis
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[*] posted on 4-9-2003 at 19:19
Garage Experiments With Trichloromethane.


Hello forumites, I bring you some info on my cheap and easy synthesis of trichloromethane.
The chemicals I used were standard 6% sodium hypochlorite solution and acetone. My bleach came from 'Chlorox Ultra', I believe, which was slightly yellow itself. I did a quick and dirty calculation from Rhodium and found out what I should use if I would like to keep it at 5% bleach. I used 6%, but I figured I'll keep some excess hypochlorite.
(Keep in mind folks, this is a 'nitro' away from Samosa's "Messy Jam-Jar experiments with Chloropicrin";) What did I use as my reaction vessel? A quart mason jar! No need for using graduations, just use the marks on the side of a beaker! I dump 500 ml of the solution into this large quart jar. I measure off 10mlof Acetone with a graduated cylinder and pour this in a film can for easy pouring. I take this out to the garage, as I was a bit paranoid about fumes being evolved. I slowly stir the acetone into the mixture with the metal wire used on those little flags people use to mark sprinklers in their yard. I stir this for around one minute and the solution is the same color as the bleach in the first place, yellowish. Then as a minute nears, the solution turns foggy, yet still yellow. Nearing 1:30-2:00, the solution starts turning white and foggy. At this point I felt the side of the jar, it was quite hot. After some odd expression I probably muttered, I ran to the kitchen, where there was an ice cream bucket left over from a party or some thing. This I quickly filled with cold water and placed the jar inside it. When I continued stirring, it felt almost 'frothy' when the wire was spun back and forth in the solution. I later determined this is when the trichloromethane is being formed. I kept stirring for around 5 more minutes and looked at the bottom of my jar. Upon tilting on its side, there was a nice, clear layer happily sitting on the bottom. Agitation of this blob provided tiny bubbles raising up from the rest of the mass. I presumed this was either chlorine coming out of solution of vaporized trichloromethane from the heat. I decanted off the whiteish liquid on top into the icecream bucket with the water. I then suctioned off the chloroform off the bottom. Hurray! The scent is similar to DCM, and there is really no flammability. A bit soaked in paper towel and held to a flame will sizzle slightly and occasionally give off a darker smoke/vapor. I do not know if this is the papertowel burning, or otherwise, but at one point, I sniffed lightly the fumes rising above it and was hit with an odd sensation of burning, pain, shock, suffocation, and general suprise. Bad fumes :) . I went back and repeated the experiment many times, and found that same results could be had with little input. Use a water bath for smaller batches like this, ice would be expensive (if bought). I would add reactants, stir till it is white and cloudy and do something else. Then, come occasionally and stir a bit. I ended up banging this off quite quickly, and could do a batch in about 10 minutes. Using the above amounts, I got yields around 4-7 ml. As said before, the yields arn't great, but everything is common and most have the chemicals lying around. Improvements can be made using 10% hypochlorite solution, which they have at pool suppliers and confirmed at my Ace or 'bleaching powder' which I have not encountered before.
Enjoy!




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thumbup.gif posted on 4-9-2003 at 20:21


Good stuff Haggis, and it does actually remind me a lot of my own experiment w/ Chloropicrin :D.

A few suggestions, though. Cooling is very important in this reaction. I don't know the correct temperatures off the back of my head, but I do know that higher temperatures cause Chloropicrin to decompose... And be careful with heat, decomposing Chloropicrin has been known to produce Phosgene.

Was the blob at the bottom of the mixture the Trichloromethane? I didn't understand that little section.

As far as the Hypochlorite solution goes, I was wondering if one could obtain concentrated Sodium Hypochlorite solutions from Calcium Hypochlorite sold in pool stores:

2 NaOH + Ca(OCl)2 --> 2 NaOCl + Ca(OH)2

If this works, you might be able to improve your yields. Of course, if this is used a means to obtain Trichloromethane as precursor, you would be using much more of the reactants; and with the cost of the reactants so low, the yields are tolerable.
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[*] posted on 4-9-2003 at 21:55


I am interested in trying this out myself, experimenting with it quite a bit. My main interest is in experimenting with the different concentrations yielded through varying methods of manufacture, and the effects of those concentrations on the subject. I have no equiptment at all, so I'll have to run around town tomorrow morning and improvise with whatever I can round up. The main thing is the vacuum used in "sucking out" the bottom portion.

Now, with the manufacture of certain chemicals, the bottom portion cannot contain any part of the top portion. If they are dumped into the container together, you have yourself a nice purple cloud where your house used to be. Is this the same with tricloromethane manufacture? In other words, how carefully does the vacuuming of the bottom substance need to be watched? Will it continue to batch if a small percentage of the top portion is vaccumed out as well?

Excellent garage experiment, I must say, and very, very applicable! :cool:

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[*] posted on 4-9-2003 at 23:19


I don't imagine you would even need a vacuum pump to do this. Haggis did this whole experiment using the "jam-jar" methods, which I find very useful.

So, archaelus, if you would like to experiment, all you should need are the reactants, a mason jar or two, and an eye dropper. The eye dropper would be used to extract the bottom layer of the mixture; at least, that is how I did it when I wanted to extract a layer of Chloropicrin.

I don't think that having a bit of NaOCl solution mixed in with the Trichloromethane will cause a colored-smoke disaster in your house ;) ... however, if you want to use it in other reactions, you may want to find some means of purifying the Trichloromethane.

Also, I forgot to mention. If you will be storing your Chloroform, make sure you add a bit (i think 1-2%) of Methanol to it, and keep it away from direct sunlight! If you fail to do this, dangerous Phosgene fumes will develop at the top of your bottle- ready to harm you as you open it. The methanol retards this process.
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[*] posted on 5-9-2003 at 03:01


does anyone has some information on trichlorethylene ? i have about 3 kilo and i don't know what to do with it ...
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[*] posted on 5-9-2003 at 08:32
it's useful


Use it in place of other halogenated solvents, if you just want to dissolve things. If you can build better apparatus than I, or are simply cleverer, it should be possible to convert it to chloroacetic acid. Industrially, this is done by hydrolyzing it with 70% (IIRC) H2SO4. I tried to convert myself, but industry works at higher temperatures than I can (since I don't have any pressure vessels), and I was tragically forced to cut my experiments short by distractions like "school" and "moving." I still think it's a promising area of investigation, since chloroacetic acid has numerous interesting uses.
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chemoleo
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[*] posted on 5-9-2003 at 09:21


shadeT - trichloroethylene - sniff it a bit and u know what u *could* use it for :)
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[*] posted on 5-9-2003 at 10:53


well it does have a realy fine smell ... ;) nice for sniffin' ... and polverone , thanks for info
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[*] posted on 5-9-2003 at 12:56


As a followup, I will say that the layer on the bottom was indeed trichloromethane. Also, I will say to stuff the stuff in a glass bottle, as it corrodes plastics containers nicely. With this experiment, I acutally found a use for my products, and a productive, legal one at that! A friend's little brother had to collect bugs for his biology class. What else to use for the killing jar besides chloroform? It works very nicely, and is a lot quicker than the 'acetone free nailpolish remover' (ethyl acetate) that they told them to use. Just a side note, using the method I outlined, a 96 ounce bottle of 6% bleach will yield around 50mls. This is around a dollar, raw chemicals, including the acetone.



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[*] posted on 5-9-2003 at 13:25


Alright, I've obtained the materials, and I am about to start cooking!!! In picking up 10% hypochlorite, I noticed tablets that were about 70 percent hypochlorite. Now, that made me smile.:D

I think that using tablets has been brushed upon, but not fully discussed. Assuming that such is the direct active ingredient, the more the better, right? (I told I'm an amateur).

As far as cooling goes... what is the max temperature I should let it get? According to Haggis, simple cold water will do. I'd really be annoyed if I killed myself trying to make this.

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[*] posted on 5-9-2003 at 13:30


No, you wouldn't be annoyed, you would be bored to death. :)



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[*] posted on 5-9-2003 at 13:49


Using cold water will work fine, but keep in mind to 'feel' the temperature and make sure it doesn't get too high. High temperatures shouldn't kill you, only reduce your yield. I've noticed that during general handling and for some reason decanting, I occasionally get a stinging in my eyes. Take care of this.



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[*] posted on 5-9-2003 at 14:01


Alright, the materials are batching right now! It is going through the phases you mentioned... it is currently at the yellow, milky stage. I was surprised at the violent reaction when I initially mixed the acetone with the hypochlorite.

Now, I don't know if I measured off exactly 10 mL acetone. It may have been closer to 15. What results can I expect from this?

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[*] posted on 5-9-2003 at 14:05


If too high of a temperature will more or less make the materials batch more quickly, then will too low of temperatures slow or even halt the batching process?

And does trichloromethane cause skin irritation?

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[*] posted on 5-9-2003 at 15:05


Ok, experiment complete and failed. Rather than ending up with Chloroform, the bleach and the acetone just seperated. The mixture never turned white and nothing got frothy. However, at first touch of warmth on the glass, I put the jar in icewater, which may have retarted or halted the batching. I think I'll wait 2 minutes next time before dunking... let the mixture get nice and hot.

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[*] posted on 6-9-2003 at 15:09
conclusion


I was wrong!!!

Due to the fact that the froth wasn't quite as frothy as I had imagined or that the solution hadn't turned as white as milk, I assumed that the acetone and sodium hypochlorite had seperated, the acetone moving to the bottom of the jar. I extracted what I believed to be the acetone, just in case, and putting it on a rag and taking a good inhalation, ther was then no doubt in my mind that the semen-looking substance was indeed trichloromethane.

Having never been kidnapped by use of chloroform, I was surprised at my reaction to the vapors. I was drawn to it, wanting to hold it to my mouth and let myself drown in it. Then again, that could just be my chemical dependancy kicking in. However, if this is normal, I can see why it is so effective as a knock-out agent.

Thank you all for the suggestions and help. This was indeed a worthwhile experiment. I see I'm going to have a lot of fun on this list.

Archaelus
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[*] posted on 8-9-2003 at 20:15
conclusion #2


Having manufactured a useable amount of trichloromethane, I stored it in a clear glass bottle with a cork. Aside from noticing the cork being eaten away by the fumes alone, there was another interesting observation: the product had changed color and texture. Previously, it was a bit white and a bit viscous (sp), and looking at it today, it is transparent and a good deal of the viscosity has gone down. I was storing it in a hot garage, and think that such may be the reason for the change, although the only warnings I've come across is to not expose it to excessive sunlight or oxygen, as such produces phosgene. At what temperature should chloroform be stored?

As far as the applications of chloroform, how much is needed to "knock out" an hypothetical human subject weighing approximately 120 pounds? How long does it take to "kick in"? And how long until they naturally revive (assuming that they are not in the 1 of 1000 that die from it)?

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[*] posted on 8-9-2003 at 20:47


Hmm... To quote material safety data sheets: As part of good chemical hygiene, unnecessary contact with any chemical should be avoided! ;)

I would not go about trying to breathe in Trichloromethane to see the results... While the "ouch" test is good in some cases, some compounds can cause brain damage or death if you try to huff them! Surely there are other ways to test if you have Chloroform- none that I can think of off the back of my head though.

I don't think that Chloroform is the best "knock-out" chemical; I remember NBK2000 talking about a time when he held a rag of Chloroform to his face for a minute, breathing deeply, and he was quite conscious.

Then there was the time he got a little dose HCN, and was knocked out instantly. But of course, managing HCN doses seems a bit more tricky than doing the same with Chloroform :P
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[*] posted on 9-9-2003 at 09:41
deep breathing


I wasn't planning on experimenting with chloroform on myself. It can cause brain, liver, and kidney tissue damage (according to various sources) as well as the possibility of death, so since I like myself more than I like anyone else, I've found someone else to test it on. It's amazing how self-destructive some people are, so willing to do anything for a simple thrill or sexual fantasy!

I haven't been able to find anything on nbk2000... the only site containing anything having been shut down. Any suggestions?

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[*] posted on 12-9-2003 at 10:47


no suggestions- but I just remember a story he told on E&W, about his own little adventure with Cyanides...

He dropped a tiny amount (unmeasured) of sodium Cyanide into a test tube, then poured in HCl. He held his thumb over the lip, and mixed the reactants a bit. But, the pressure built up quite quickly, and caused him to lose grip with his thumb, thus causing a puff of HCN to go straight up his nose.

He passed out for a few minutes, but came out alive. The good thing about HCN is that it doesn't cause long-term injury- if you recover, it's as if nothing happened :D. Just make sure to get fresh air.
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[*] posted on 14-9-2003 at 13:28
Trichloromethane


It may interest you to know that trichloromethane can be oxidised in air in the presence of light to carbonyl chloride, with the elimination of hydrogen chloride. This may be the cause of that burning smell in the first post. COCl2 is not corrosive or dangerous until it contacts moisture. It will then hydrolyse, producing two HCl molecules and one of CO2. Just a tip should you want the phosgene, use an oxidiser or bubble oxygen through the TCM and then cool any gases coming off well below 8*C. The liquid coming off will be phosgene. This rcn. goes slowly but is worth it if next door has a pesky, apparatus upsetting cat.
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[*] posted on 14-9-2003 at 17:34


well, for our purposes, COCl2 is always dangerous since our respiratory system seems to be lined with moisture :).

But, I have been looking for a route to Phosgene, other than the CCl4 method or CO + Cl2- both of which are impractical for me... I have considered oxidizing CCl3, and so I thank you very much for this new bit of information! I now have a new reason for Chloroform.
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[*] posted on 14-9-2003 at 18:30


Just for completeness I would just like to say a word about the reaction. It is a haloform reaction, it oxidizes methyl groups directly attached to the carbon that makes up the double bond to oxygen in a ketone. It takes place under basic conditions in the presence of halogen so the hypochlorite salts are perfect for this. When the reaction is over you have the oxidized ketone minus one carbon which in the case of acetone would be CH3COOH but you could use say Methyl-ethyl ketone and get CH3CH2COOH so it's good for making carboxylic acids (In the above reaction they would end up as their sodium salts) so the overall reaction goes:

CH3COCH3 + 3NaOCl ----> CH3COONa + CHCl3 + 2NaOH

With some NaCl and such thrown in for flavor. By the way, I don't think the above reaction is entirely correct... I've got different numbers in my notes but I don't know where they came from. I'll update my post if I find the source again. So basically you can use any basic enviorment with free halogen thrown in, so you can get bromoform and iodoform but I don't think fluoroform, free fluorine would not take well to an aqueous enviorment, also it is a decent way to make carboxylic acids.
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[*] posted on 20-9-2003 at 13:21


Today I tried to make chlorform, accident happand...

In a 500ml erlin flask I added 100grams of Ca(OCl)2. I then added 60ml of water to moisten it up. I added 44ml of acetone, I have a rubber stopper, with 5mm of glass tubing attached to it into a 125ml receiving flask. When I added the acetone in I quickly put on the stopper. It was a violent reaction, before I knew it the stopper blow off, and I was sparyed with calcium hypochlorate, I was lucky I wore my goggles, and i was engulfed in a cloud of chlorfom and acetone, I got away, but I felt really weak and dizzy. After an hour later I'm still feeling the ill effects, feeling lightheaded, and have aheadach.




TNT
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[*] posted on 20-9-2003 at 18:47


Here's what I think you did wrong, TNT. First of all, you had an 11.6 M Ca(OCl)2 solution- that is very strong! On top of that, you added your Acetone all at once (unless I've misinterpreted what you wrote). Bad idea! Don't rush the reaction, especially with such a strong solution. Take your time, and be sure to keep the reaction nice and cool.
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