Making Methyl Iodide
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- Опубликовано: 18 июн 2016
- Hey guys, today we make a little bit of methyl iodide (iodomethane) using methanol, red phosphorus and iodine.
I plan to use this in the future to synthesize caffeine. If you guys have any suggestions on how it can be used, let me know!
References:
• Chemplayer video: • Video
• Erowid: www.erowid.org/archive/rhodiu...
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I have a chemistry exam tomorrow and I'm sitting here watching this... Am I being productive or am I procrastinating
Both :)
+Nile Red well, I hope I find something that can help me with my other exams as well then :P, as always great job with your video, you always have something interesting to show everybody
It is always a good day when Nile red uploads a video.
im so keen to see this whole caffeine reaction!!!
That was neat. Thanks again. Also, the red phosphorous from match books sounds cool. My vote is for that sooner than later.
-That appears to be quite the ambitious synthesis pathway :D I have a 1,3,7-trimethylxanthine tattoo on my right shoulder and look very much forward to seeing your progress, fellow chemist!
you put the caption of red phosphorus instead of 83,3g iodine
ughhhhhhh
+Nile Red hhhhhhhgu
+Nile Red uurrrrrrrrhhhh
make an overly complicated siphon pot of coffee like in breaking bad
Great video, as always. I was wondering if you were going to finish your synthesis of 1-octen-3-ol, cause that compound is really interesting.
There is a story behind that. I made the acrolein but it polymerized. I am taking a different route to it now. It is a little more interesting.
Nice! I'm looking forward to that.
@@NileRed
Can you try making methyl iodide via the Hunsdiecker decarboxylation ?
The reaction is simple:
Dissolve a lot of iodine in carbon tet and start adding silver acetate powder. CO2 will start bubbling out and at the end you should have only iodine, silver iodide, methyl iodide and the solvent.
for a phosphorus-free route, wikipedia says Iodomethane can also be prepared by the reaction of methanol with aqueous hydrogen iodide
Just a question, if that filter was gone anyways, couldn't you try and oven-dry it and then burn out the phosphorus? M?ight be a bit extreme but you could end up with a clean funnel :D
The best method of cleaning a glass contaminated with red phosphorus is treatement with strong nitric acid (33% and more). Hot phosphoric acid destroys glass very well, so you don't have to burn red phosphorus!
Gonna look pretty suspicious when I order a load of Iodine and red phosphorous.😂
You can actually use aluminum instead of phosphorus for this reaction, although yields are lower. I believe chemplayer did a video on this.
+Chem Player huh do you have a vid about that
are you a chemist?
+Forjam firs of alll im 13 but im an amateur pro one
the amateur scientist #Oxymoron
Nile when do you do the video of Kclo3 elektrolysis? Ive been waiting for it a long time.
lol following recipes from Erowid xd nice one dude
Reacting iodine with red phosphorous to make something with the word "meth" in it...seems a bit meta.
Yes because everything with the word "meth" refers to methamphetamine... 🧐🙄
@@MadScientist267
Methamphetamine is simply amphetamine with an extra methyl group. Don't ever mess with it. Half the people in US jails are there because they messed with, sold, transported or otherwise had something to do with methamphetamine, this according to a criminal lawyer on RUclips.
“I got part of this from Erowid” yeah buddy, this is def part of THAT recipe.
@@karlbergen6826 And hence why iodine and phosphorus are controlled substances
he's probably gonna react his methyl iodide with his prescription amphetamine to form methamphetamine
Great video as always! Mercury distillation? Sounds like fun! ;)
Scary as fuck
Maybe you could clean the sinter with nitric acid (it should react with P to form now water-soluble phosphoric acid).
Another idea is using hot ethanol as P is slightly soluble in it.
But it might not work for physical reasons - polymerized material stuck in fine glass might not react adequately.
Red phosphorus doesn't dissolve in ethanol (and other solvents), but nitric acid would be a good choise for cleaning. I use it for the same purposes.
Does in carbon disufide.... But avoid that just get a new frit.
1:50 it said you added red phosporus instead of iodine. Great video though!
Probably the least sinister reaction you could've done with Iodine and Red Phosphorus.
To clean red phosphorous from your funnel, just add some dissolved iodine(in alkanes/alcohols/ethers/toluene/acetone/etc). Good as new :)
That sounds like it would work.
thanks for the video, great job as always, i'll be realy happy if u show how to make some quaternary ammonium cation with this, like tetramethylamine or another more interesting quaternary ammonium cation.
Do you have a use for tetramethylamine?
+Nile Red nop, but I read some article on the quaternisation of amonium cation but i'm curious to see how to proceed to achive the réaction.
6:40 Isn't cleaning glass fritted filters the specific purpose that is the best reason to use Piranha solution? (H2SO4 + H2O2, since it can remove even tiny amounts of things like carbon and phosphorus without damaging the fine structure of the glass filter at all)
Is there a reason why you used 8-9x as much red phosphorus as you need? I mean if you can recover it, fine, but if you know that the reaction will only consume like 5 grams, then maybe you add 10 grams to have plenty excess, but not 42 grams :P
Another great video.
I have a question regarding safety.
It is hard to tell from your video but do you use a fume hood or just a well-ventilated area?
Do you take any extra precautions for this substance than you would for most other organics you make?
I am hoping to make some methyl (or ethyl) iodide for a Grignard reaction to make tertiary alcohols from ketones. However reading around about the toxicity it seems like these compounds are nasty ("highly toxic dimethyl mercury can be produced if allowed to contact mercury amalgam" for example). I do wonder if some of these fears are a little overblown but regardless, I don't have access to a fume hood so was hoping to limit my risk by conducting outside and making it on the fly for use in the Grignard. Do you have any thoughts on this?
Sorry its a little wordy but would appreciate your feedback on this :)
Your concern is well justified. I would make the methyl iodide out side and keep it away from mercury. Methyl mercury is extremely dangerous but doing Grignard reactions with methyl iodide should be safe if you take care not to breathe the methyl iodine. The creation of the Grignard reagent is quite exothermic. Start on a small scale and take care it doesn't run away. If you do lose control get away until things have settled down. Wear gloves and googles.
You could try to create an organic superconductor, I mean you probably couldn't get the pressure or temperature required to activate them but it would still be cool
I relate to this chemicals description sadly all too well
hello nile red
show us how to make the materials of the nickel iron batery!
That's all that needed to be sustainable and cheap energy!
best regards
I would love to see an alkylation of an alpha-carbon using NaOH in PTC conditions. Would that be a possibility? Acetophenone could be a possibility substrate with only a single alpha-carbon and a high enough pKa to make normal bases too weak for deprotonation.
hi nile red i love your videos
I am glad you like them!
nile red i have a question. on my newest video i put tunstic acid on aluminium foil and it turned blue. do you know what it is? thanks :)
Could you extract theobrymine if it's possible with your tools?
You can work Grignard synthesis with it. Prepare Anisole from Phenol
I am actually going to do that. I just dont want to use it all up and have none left to make caffeine
Great videos, wondering why use 40g of the red phosphorus when you can calculate to see you only need 5g?
He's using it to make sure that both of the other compounds are fully consumed. It can be recovered and recycled later.
So interesting to see you handle red phosphorus that easily, after seeing white phosphorus in action.
Red isnt gonna react with air like the white, its super inert as far as the P chemicals go.
Yeah, I can see that, but the fact that it does!
awesome video, can't wait for the caffine synthesis from scratch. may I have your patreon info i would like to support.
NileRed - FYI, At 1:50 you say you added iodine, your notation in the upper left says red phosphorus
Could you do a synthesis of nitrogen triiodide?
Any chance of Sodium Azide or Nitroguanidine?
Airbag special :D
I Like your videos
Synthesizing caffeine from maleic acid? Wow! You've become Very ambitious.
would there be a by product of hydrodic acid ?
where the heck did you get the red phosforus
Maybe you could use it with tryptamine and IPA to make some unnamed quaternary salt?
😆
Wonderful video, and actually might be helpful to me for a future synthetic step in my research.
Question: Why such a large excess of red P? Was it intentional or a broad overestimation?
Interesting idea but be very.careful not to breathe the methyl iodide. It is a methylating.agent.
A menthol synthesis would be pretty darn cool
Alcoholic fermentation creates some methanol. For this reason never make your own liquor. With the right yeast variant you can get a lot of methanol
@@karlbergen6826they said menthol not methanol
hey nile ,
can you pls let us know how to work with a Roto-Evapourators !!!
Can this be used to form CH3+ and I- in solution?
You have to mention that Methyl Iodide is a very strong carcinogen and you have to wear a respirator or work in a fume hood. A well ventilated area is definitely not enough!
meganie8 I personally love alkylating my DNA. How else are we supposed to get super powers?
I was wondering... i have a couple bottles of ethyl iodide that have decomposed. Can i use this methode to turn them regenerate it?
And is there any substitute for red P in such reaction?
Hi just wondering if you could make Ammonia nitrate from electrolysis of ammonia
Shouldn't Calciumchloride displace the iodine with chlorine in methyl? Isnt the C-Cl bond stronger than the C-I bond?
You should teach you how to make sodium hypophosphorus. I'm going to use it to make hypophosphorous acid.
Will you ever make anything with the lithium hydroxide
Did you finish this project? Would love to see it
thnx much .. can you make a video to methylation imidazole by methyl iodide to produce 1-methyl imidazole
+ NileRed
Can you please make a Video how you make this structure formula?
It's supposed to be useful in producing quaternary amine salts from organic acids.
what would happened if you flash a small sample with camera flash ?
It blows up.
...oh wait, did you mean
with the light from the flash?
1:50 added 83,3 gram of iodine, but in top left it says red phosphorus
New tour of the fume hood please respond
Nice video!
If your doing trimethylamine in future, could you also do dimethylamine?
And it would be sooo nice to see Willgerodt rearrangement in action.
hey Nile red whats a good site to purchase equipment and also all sorts of chemicals i do live in Australia so i wont be able to order many things but O well
Can it be used for synthesis of nitromethane for RC fuels? Can you advise?
Usually in lab nitromethane is made by reacting sodium chloroacetate (CH2ClCOONa) with sodium nitrite (NaNO2) in aqueous solution, but sodium chloroacetate is a pretty poisonous substance and it may be hard to get.
NileRed can methyl iodide be used to make dimethyl mercury?
Use the CH3I for synthesis of iodine containing stuff?
What would happen if you tried to clean that filter with piranha?
+Nile Red why do you put some Copper in the bottle?
Can you convert phosphoric acid into elemental phosphorous? A video turning a few liters of Coke into a few grams of red phosphorous would be interesting.
1) in coke there is really few phosphoric acid. Maybe 300ppm. By extracting it from coke you would use at least 20L of it to recover 5 ml of phosphoric acid. It would be better extracting phosphate from fertilizers or bones.
2) to reduce the phosphate back to phosphorus you need to use SiO2, elemental carbon and obviously the phosphate. This seems easy, the only problem is that the reaction needs to run at 1500°C.
The immediate product is white phosphorus which is extremely dangerous. To convert it to red phosphorus heat it with a iodine crystal. Work with red phosphorus. You'll live longer.
Can you please tell me where a can get those pyrex jar? I cant find them on ebay...
For methyl iodide
What happened to the H3PO3, can anyone please explain this to me :( ?
when you add iodine for the first time your label says red phosphorus. you might want to throw an annotation over that for ppl who don't listen lol
I did change it! I wish i noticed it before uploading it though :(
It happens
what is that stir bar made with? Nothing can damage that:D
Teflon i guess
Ginfio Drebfa Ah I see...
Justo Talkalottashit Sure it is :-D
Teflon
Polyperflouroethylene , also know as Teflon , is used for its strong chemical resistance to stir all kinds of mixtures
Just wanted to let you know there is a typo at 1:50. You say 83.3g Iodine, but your caption at the top left says 83.3g Red Phosphorus.
Yup, too late now though :(
Would using Ethanol instead of Methanol yield Ethyl Iodide?
71%? Use h3po4 and k/na I and methanol and get 80%. Also use dry ice calcium chloride water for the condenser, it improves the yeild. I think this method can almost get 90 percent yeild if proper cooling is used. Anyways good video
Wich hydroxide -potassium or sodium, to get 90percent?
@@johnadams347 sodium/ potassium iodide not hydroxide
You should keep it in a brown container and then seal it with parafilm.
That will both prevent escape and decomposition.
Method you found on Erowid? Can you do a P2P synthesis?
So how come you used phosphorous in that much of an excess?
At 1:55 it says red phosphorous instead of iodine
What's the point to add that much phosphorus @ the beginning?
Suggestion: making 2-Ethylanthraquinone to make Hydrogen peroxide by the anthraquinone process, i want to find information before but i only find very simple one... i think it is a good topic for your video.
Ill look into it, but it might be a little tricky.
Methyl Iodide is also used in geology for separating minerals.
I did not know this
Erowid huh? I bet you are cooking up some 2-CX compounds for some extra pocket change
New patreon perks I guess.
Gotta donate fast.
Why would he cook that when he could just replace the methanol in this synthesis with pseudoephedrine and make two ounces of meth?
Alex Trump and i think hydrochloric acid
No, HCl is not used in the birch reduction of methamphetine. It is however used after the reduction to turn the freebase drugs into hydrochloride salts.
I think most biochem/orgchem researchers have at some point bumped in to papers published on erowid. The lab where I worked (legal pharmaceutical drugs) used several of their articles to improve yields in intermediate steps. The industry is quite aware that illicit drugs are a part of their field... and despite the fact that *some* substances cause harm, the science behind them is very fascinating and often helpful.
Did you scrape all that red P or did you manage to buy it?
I bought it. That would've taken forever, ha
+Nile Red I know. that's why I ask. lol. where did you get it? Red P is hard to find. Ali?
I may be some sort of late, but why don't you just synthezise your CH3I out of CH3OH and HI? As far as i know, this should give quite a nice SN2 reaction resulting in H2O and CH3I.
Anyways very nice synthesis you did there.
HI is very easily split into hydrogen and iodine. If this happens with red phosphorus the iodine is reduced back to HI.
did u unlist this video then list it again because u are going to synthesize caffeine now?
You're allowed to own red phosphorus in Canada?
STOP dropping in your stirbars!!!! The first time you break the bottom of an expensive multi-neck reaction vessel is not the time to learn this. Turn the flask sideways, place the stirbar in the neck, and right the flask. Now begin adding reagents.
But where did the phosphoric acid go?
Where did you get that much red phosphorous?
Exactly what I waswondering lol, I'm pretty sure +Nile Red lives quite close to me, and I'm not sure where I would get that much phosphorus without some paperwork.
Even in Germany (where almost every fart is restricted) you can easily buy red phosphorous at Amazon or Ebay. Red P is not assigned as a dangerous matter (apart from it's high imflammability). I payed about 30.-€ for 250 g.
I know that Phosphorous can react in a desasterous way, especially in the "Armstrong Mixture". But red P can be sold/purchased without any restrictions (as far as I know), apart from the fact that the buyer has to be reached the age of concense. Red Phosphorous alone is neither explosive, nor toxic, nor a CMR-substance nor an oxydizing agent.
Where are you from?
In Poland Red P is about 20-40$ per 1Kg
0:44
where's the synthesizing caffeine video?
Annotation @1:46 is incorrect. Just in case no one caught that yet.
Extract malic from apples please!!!
Pls teach me how to make C10H15N
Make dimethylmercury with your CH3I. :P
KazooKid always has the best ideas
+NileRed Sure :P
sure why not. you make the video? i for my part want to keep Nile alive. probably the best chemistry channel i´ve found so far. Nurd hardly talks about mechanisms and chemplayer don´t really do that as well.
Metalhammer1993 it was a joke. i love nile too
@@NileRed when will the video come or is it out
If I'm not wrong, with I-Me you can't obtain a secondary amine. I mean, it's a very fast reaction, you will have a pretty precipitate, as a quaternary amine salt... If you want to make a secondary amine you need to use Formol with NaBH3CN or for a primary : use the Gabriel Technic, you see ? So @0:26 I think this is not accurate :p let's discuss about it
Real world use..at least in my world. Specific Gravity liquid for identifying gemstones.
Stupid question... Why use so much phosphorus in the reaction if it's not being "used"?
It is used in excess to make sure that all of the iodine is used. Both methanol and red P are used in great excess. It is probably much much more than necessary though
Could you make some organometallics with this? Like dimethylzinc?
Of course you can make organometallics with this. Don't know about dimethylzinc in particular though
+neovictorius yes I know,but I was curious if perhaps nile himself could try making any organometallic compounds :D wiki mentions that Zn(CH3)2 is usually made with methyl iodide.
Oh, I thought you meant as a general question :P
Why is that you added so much phosphorus compared to required amount by molar ratios? Also incase of carbon stuck in glass filter couldnt you just wash it with H2SO4/H2O2 mix? Maybe it would apply for phosphorus too.
It doesnt work for carbon well...I still have a dead filter from a previous video where i filtered carbon.
You could also try a mixture of concentrated nitric and perchloric acids. I once been to a lab, where a guy was using this to clean out really clogged glass filters.
+Madarpok I don't want to be anywhere near somebody mixing Nitric and Perchloric Acids. Nope, Nope, Nope.
Then again, the guy who does this is well known for not wear gloves at all, unless he is doing something exceptionally dangerous. He wore gloves for this one, I think.