Chlorination of Isobutene: The Gas Phase! 1-MCP ep02.2
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- Опубліковано 28 вер 2024
- We have another attempt at making methalyll chloride, this time by reacting chlorine and isobutene both as gases at room temperature.
Will the water help scrub out the HCl byproduct? Will removing UV stop radicals ruining the reaction? We find out.
J O H N B L A C K S U P E R C H E M I S T: / channel
Subreddit: / explosionsandfire
Music: AFX (Aphex Twin) - 3 gerald Remix
Interesting to watch and I admire your perseverance.
I’ve often wondered how the early chemists were able to figure out definitively what they had created with crude instruments. An NMR would be great here but few of us amateurs have one.
Yes early chemists are certainly very impressive, working out the composition, structures of things, without any 'technology' at all! Thats always the thing keeping amaetur Chem going, the idea that people back then did it fine, therefore so should we
@@ExtractionsAndIre I'd really like to see that kind of content - figuring out the composition of unknown chemicals.
An enema?
Honestly I get really excited when I see your videos.
Me: [sees that you drew methyl acetylene with an angled triple bond] **TRIGGERED**
Looking fprward to settling down in front of this vid.
This is proving to be an intriguing (and original) series.
The most impressive aspect of your channel is you achieving these reactions with a lab that is apparently situated in Crocodile Dundee’s bush camp
🤦♂️
super cool. Didn’t work. But super cool. Thanks for the shout out. Thats awesome.
Keep it up. I learn a lot from your videos. And even more from the discussion after.
12:24 I was tempted to get some teflon tubing, but after seeing your troubles with it (not just in this video, many others, understandably), I held back. I feel like there must be _some way_ to make it easier to work with... Maybe use heat to preform pieces into specific shapes that can be joined together with joints or something like that.
I consulted the Google Gods and most agreed upon recommendations made it sound like working with it was similar to handling wild anaconda in the jungle... "First, mechanically wrestle the tubing into place; then tie it down using cable and C-clamps making sure to use enough".. lol. I was thinking "yep, that sounds about right".
You'd think there would be some tubing that was only coated on the inside with teflon and would be more flexible, but I didn't find much that seemed to be worth it or any better than full teflon tubing.
There are other types of hoses that can work. I can't remember if Viton is Cl-resistant or not, but there are lots of weird and wonderful polymers/elastomers made by all sorts of chemical companies. I actually have this floppy disk from the early 90s from 3M called "3M Elastomer Selection & Design Guide". It's fun to look through. It's more or less an advertisement for their fluorinated elastomers, but it contains just mountains of charts about which chemicals each type is compatible/incompatible with. Just fired it up, and they are advertising Fluorel, Aflas and Sylon. For use with chlorine, it recommends Fluorel for seals and tubing! (EDIT: Wow, after googling for Fluorel, I realized that it's just another name for Viton! So there ya go.)
Live audio all the way through.... amazing!.... I never acquired that sort of skills, doing experiments plus talking are just too much work to be done at once.... btw is your tube doing ok after this, mines severely damaged after undergoing similar abuse
Aussie Chemist The tube is wrecked, lost all flexibility. Might be good for one more chlorine run. The isobutene tube is okay except for the end that was in the chlorine, I'll have to amputate that bit.
And practise man, far too much practise.... And heavy editing
Extractions&Ire I’ve been looking for the ultimate tube for all environments, but there seems to be none, tried silicon, ployethylene.... none of them were invulnerable, PTFE is good but not exactly flexible... any good suggestions?
Aussie Chemist The best tubing apparently is a thing called Viton. The inertness of Teflon but actually has flexibility. No always easy to find though and of course.... Expensive. It might be cheaper to keep replacing rubber tubing, rather than buying real good inert stuff
@@ExtractionsAndIre awhile ago I wanted to get viton gloves for working with very concentrated acids and bases. They were just too damn expensive so I ended up settling for butyl rubber
I love these videos. Good job! One of these days you’re going to get the methallyl chloride thing. I had a chuckle at the mention of JOHN BLACK SUPER CHEMIST. That guy is great and I love that you put the super hero effect on when you said his name.
Love your videos both here and on Explosions&Fire.
Please keep them coming. :D
I'm late to the party here, but.... ~20 years ago in college, for a chemeng course, we were successful taking the pyridine route.
I love the interludes with the music a la chemplayer. I think they are great segues and they look great too 👍🏼
kjpmi glad you like those bits!
Even with the failures this has been an interesting series to watch so far :)
Good luck!
RIP JOHN BLACK SUPER CHEMIST
Very intriguing! (And entertaining!)
Elyjah Vasquez glad you think so!
I know he's saying NMR, but all I hear is Enema. Not a pretty picture I might add lol
Are we 100% sure this channel isn't run by Matt Parker?
Captain hindsight here. I probably would have used more dry ice, but just on the receiving flask and tubed the vapors into it. A tiny bit of antimony trichloride as a chlorination catalyst and simultaneously piped in the chlorine. I dont think the methallyl chloride will care about the HCl, in fact starting with a few drops of conc. HCl to make sure you don't end up with a basic environment.
Isn't methyl acetylene straight?
btw triethylamine may not be OTC, but trimethylamine.HCl can be made by a modified formalin/NH4Cl reaction IIRC (for methylamine synthesis). Of course yes its base is a gas at RT, but you can make a solution of it.
I would run a NMR for you. I just don't know how much shipping is from Australia to Germany and how long it would take. But as long as you can seal it well enough so it doesn't smell it shouldn't be a problem. Greetings
Nice work, gas phase reactions at home, not an easy feat.
I have a basic grasp on these things but I love your videos
I would try making methalyl bromide. Bromine is considerably more regioselective. Use NBS it will remove HBr from the system.
Awesome shout out to John Black Super Chemist. That guy is great.
like some drongo jar jar binks method just gotta make it work for you, try to realise your unique style. Like your chemical aesthetic. The Sand and the rips in the alfoil. Energetics Instability. What if you find Stable Passive? The like Red to your Blue. Work with what youve got. Love the Channel Funny and that.
video stabilization please very shakey
Good video man. :)
I think you’re making an addition of cl2 to a doble bond
It's create sodium chloride and acetic acid, pity chips weren't also a by-product, lol.
As I said on reddit, you can use TCCA instead of NCS for Wohl-Ziegler halogenation :)
I need a better username That does sound magical, I'm just struggling to find any references that says it'll work, do you have any?
Oh, now that I checked, chlorine is just too reactive for Wohl-Ziegler reaction. (but it would work with tribromoisocyanuric acid, the mechanism is the same as with NBS)
The double bond is annoying, it would be nicer to not have it, do a chlorination and then introduce it later, but oh well, the literature says this should work and I feel we're closeee
Yeah, that's what my previous procedure did but these bromoisobutene isomers are a pain to separate.
But tribromoisocyanuric acid should be easy to make:
1. Make dilute hydrobromic acid like nurdrage
2. Slowly, with cooling add dilute hydrogen peroxide to make a mixture of bromine and water
3. Drip in trisodium cyanurate, tribromoisocyanuric acid will precipitate:
Na3C3N3O3 + 3 Br2 = C3Br3N3O3 + 3 NaBr
Use NaOH to make sodium cyanurate, NaHCO3 is not basic enough. You can do Wohl-Ziegler reaction in chloroform or DCM.
I have to remeber celius celius
I would like to see "Chlorination of methane to for DCM"
I know this is unrelated to the video but... what was the name of the explosive made from Methyl ethyl ketone?
HV Lab methy ethyl keytone peroxide
Thanks, maybe I will try to make some of that.
HV Lab I highly suggest against it. I've made the compound and it is amazing unstable, even by organic peroxides measures. Would suggest if you're interested in explosives to start off with another one. If you're interested HMU on instagram @science_and_anonymous
very interesting
we have another language unfortunately.
create in writing,
the text of what you are doing under the video.
this could help a lot.
Thanks for watching!
I do talk very fast I am sorry, I will think about putting more text in the video so people can still understand what is happening if you can't understand a lot of the talking
much we understand - thanks.
there are only details (nuances) - it is not clear.
in general - your videos are informative.
look like it's for Chem Player ua-cam.com/channels/iU1dHvZObB2iP6xkJ__Icw.html - it's an example.
1. what substance.
2. how much substance.
3. The formula.
a short entry right in the video on the screen.
for some experiments it may take a little explanation - what am I doing? - I'm doing it.
in general - you are doing very well.
Thank you.
Remember, breaking safety rules is fine when they finally become too inconvenient. Also remember, the more times you say "I'll be fine" the more satisfying it would be for a higher power to decide to blow up your garage.
Haych
i have a new extraction idea: make H3PO4 from bones remained in the meat u eat
TM Fan ohh man, I'd have to eat a lot of meat :P
Phosphoric acid is annoying because it eats through glass sometimes... But I'll think about it!
Extractions&Ire u can probably eat more chicken wings, legs, beef/lamb ribs, meat which contain higher bone content?
also why phosphoric acid dissolve glass?
I got no evidence to support this, just a random guess: Might the water be interfering with the reaction?
(Actually, some evidence, but only remotely related): When I chlorinated toluene under UV light, water was something that needed to be excluded, since it reacts with benzyl chloride to form benzyl alcohol and hydrochloric acid, which is why it works as a lachrymator. I wouldn't be surprised if the methallyl chloride would react with it too. Methallyl alcohol (the hydrolysis product I'd guess) has a boiling point of 115C though, so it's quite a bit off. Still leaves possibility for an azeotrope of methallyl chloride with the alcohol, or the alcohol with some overchlorinated products, lots of possibilities there.
I gotta say though, it's nice that you keep us up to date and also show us some failures. Keep up the good work!
I'll bet that's what it is, the allyl group has resonance so the methyl on the allyl group behaves like a benzylic carbon hence why methallyl chloride is a lachramator
Yes I think I agree, water is probably the enemy (now that we can basically exclude UV as an issue). Water is the only thing that is there enough to completely mess up the reaction enough, that there's not even a little bit of a product in there. Not sure exactly what the water is doing, but its probably the water
@@ExtractionsAndIre hmmm
Fuck, I also had the double hose idea and it didn´t works... at least I haven´t wasted my own time on it ;)
If you are overengineering, I am underengineering :P
But yes, were you thinking of trying this yourself??
I was thinking over doing it with natural gas, with is like 95% Methane.
Or reguar Butane. I actualy asked my Prof. in organic chemestry how to stopp over chloeranting and he said that this is a rather complicated process, which isn´t to easy to do even in our labs.
BP 71c
NOOOOOO
WE LOST JOHN BLACK SUPER CHEMIST
F IN THE CHAT
R.I.P. JBSC
Tape some stiff wire such as a wire coat hanger to the teflon piping you can bend it and it stays in shape.
Get a 10 liter glass jug (used for wine). They're inexpensive.
He did say he was already uncomfortable with having 1.5L of flammable gas, not sure if he would want more volume
12:24. To bend the ptfe the way u want fill it with hot sand ( put sand in a pan in ur oven for 30 min-ish at 350f.) Then use a funnel to pour it down the tube bend it the way you want let cool and remove sand
Apparently John Black: Super Chemist's channel has been removed for "violating" "community guidelines." In other words, UA-cam is a bunch of shitdicks.
UPDATE: Apparently he has a new account, but the link given in this video leads to the old (terminated) account.
be careful when storing sensitive compounds over molecular sieves, they can sometimes catalyze the degradation of your product, for example if you leave a bunch of acetone over sieves for a week, it will have all sorts of crap in it, because the acetone started to polymerize via aldol condensation
Why? What are sieves made of?
@@filipealarza9079 various zeolites, which may do acidic or basic catalysis, eg. aldol reaction on acetone
I know this vid is like 2 years old, but I wanted to point out that just *maybe* using a strong Arrhenius base like NaOH would pretty much fuck up your whole chlorine as it readily disproportionates
Love these videos! Excited to see how it turns out!
hi
views: 0
This is so amazing, how there’s sort of a community trying to solve a synthesis like this
Why you don’t use a canister R600a as your source of iso-Butane? Seems much easier to me
(There are also some camping gas cans that contain pure isobutane - I think Coleman does sell them)
We need isobutene for this, which has a double bond in the structure. Isobutane doesn't have that double bond so can't react with the chlorine :(
Extractions&Ire f**k - That’s why my chemistry sucks - just one letter make it or brake it 🤣
Why not use t-butanol? will make more isobutene and make t-butyl chloride as a side product
so where do you go from here? it's a shame to see hard work with no product. are there any patents for the production of 1-MCP?
There are some papers, but most of them are chemical engineering type stuff... so I think we are close but its just working through the issues.... we'll get there!
I bet the mystery goop is some chlorinated rubber
"I don't do small scale chemistry" *Laughs in Chemical Engineering*
Really entertaning video and series. Dont loose your hope and keep trying :D
JOHN BLACK SUPER CHEMIST is awesome! Tom Youre awesome too! Alot of the chemtubers are great poormans chemist, backyardscience2000, full modern alchemist, and i really could go on! Lots of knowledge to spread around!
i still can't tell if john black super chemist was making meth or not. half of his videos were about making things that're commonly used to make meth, yet he never made any actual references to meth
At what point would it be the smart thing to do to try and obtain the pre-made chemical?
Depends on cost, availability, and regulatory hoops. My rule of thumb: if it costs more than a dollar per gram, either try to make it yourself, or find another way.
pv-nRT Nernst equation...
Ah, yes. My favourite.
??? He says ideal gas law wtf u mean
It's still sickening to watch, but it's because I can smell it through my screen.