Extractions&Ire - 2018-04-03
In this video we use basically all my glassware at once to mix two gases together in another roller coaster of a video French (?) Chemistry (subscribe yep): https://www.youtube.com/channel/UCaqoddvGbkSel52YmDYuw7A/ Music: user18081971 (Aphex Twin) - 24 ems-alias mgroove Georgia is cute. Thanks for letting me use ur internet
I thoroughly appreciate the quasi-ghetto glassware setup. Now you feel like a real chemist!
That setup... Holy moly.
Paul Beurich I think he needs more glassware
Yes the solution I think is just to use more glassware
@Extractions&Ire And more stir bars... Don't forget to add more stir bars!
More pumps too!
@Extractions&Ire more buckets
Definitely scratched my chemistry porn itch.
Nice work man !!
Aww. There;s that feeling you get when you throw all of your glassware at a problem and it doesn't work.
Happy dishwashing. :) And time to buy a crate of Claisens.
Seriously, I have no idea what went wrong or what the next attempt should be. I was really confident when I saw the reaction happen and even more so when you collected some lovely clear liquid. Maybe dilute the Cl2 with some argon? How much more difficult could it be to cotrol the flow rate of three gases? (gulp).
That interaction with the sulfuric acid surprised me though. This isobutene seems to be a strange beast that doesn't like to play by the rules.
I would say check your isobutane.. maybe it has some crap in it... also try to use clean sulfuric acid, with organics you never know
Are you entirely sure your Isobutanol is Isobutanol?
Matt Hunter my tert-butanol I'm sure of. The isobutene gas... Well, the only real proof is that we know it has a boiling point a couple degree below zero, because we could only jusstt condense it with -10 degree water but could easily do it with dry ice. We also know that it's not miscible with water, and some came over with the isobutene in the first video and formed a separate, more dense layer. So nothing (apart for the whole experiment not working) points to the fact that the gas we're making isn't isobutene, but yes it's something to consider
Oops, yeah lol, I was researching alternate methods and forgot what you used.
"Aggressive"... the tone you said that... hilarious!
16:57 Is the oil soluble in the isobutene? (if not, then obv a sep funnel would help you separate out the oil contamination)
I’m far more amused by the reaction taking place in a Claisen adapter than I ought to be.
tehlaser; I also thought that about the time Nurdrage basically made a UV-catalysed internal combustion engine inside of a claisen adapter (he was also chlorinating something... Coincidince? I think not!).
Music straight out of early 2000s educational videos 😩
Sounds like something ChemPlayer would mix with sinister undertones. Quite eerie in combination with the shots at night.
Sounds like the soundtrack for the old conan the barbarian. Lmao
Yeah alkenes react with concentrated sulfuric acid to form carbenium ions which afaik can react with further alkenes to alkylate them. I guess it can "tar" fairly easily.
Even if it doesn't always work out, I freaking love your videos and I hope u never stop making them!
Damn, I really thought you had it this time. With exclamation mark at the end of 3 in the title and the the visual result from your setup. I'm no chemist so I can't give you any advice, but I do love your video and commentary so I hope you will keep up your curiosity for this syntheses and succeed.
zubmit it looked so promising :( but glad you enjoy the videos despite the lack of chemistry background, I love hearing that from people :)
thanks for sugesting the french channel. seems really interesting
Btw isobutene is readily available at car climatisation hardware stores in small and larger gas tanks 750mL up to 8L i think. 750 mL of high purity isobutane bottle was 2.5 times cheaper than 10 mL of tertiary butanol
Did you do a 4th try yet? Perhaps trying a known source of dry isobutane and flowing an excess instead of having excess chlorine?
Oh man, I was so happy for you; I thought you had got it. It did look promising. I really liked the flow of your setup. Seems like it should have worked. I know the feeling of losing your hard earned product to some ham handed accident. Is it at all possible that the tubing introduced some contamination? Can the small scale be a problem?
Never knew a "y-adapter" had a real name XD the undergrads at my uni use them a lot!
5:30" 3 Way Joint? Bob Marley would be proud of ya! loool
try to ask some university professor if he can give you some advice… maybe you will find out somenthing
I was like a yeah that's looking good pretty professional up until 5:23 and lol what is that blue thing!
Bravo man...that’s quite a setup and was very cool to watch. Excellent work
Are you just getting Cl2 addition across the olefin? You want to promote a radical mechanism without adding to the double bond. I know that the textbook method for allylic halogenation uses NBS. NBS seems like it should work, provided that you can accept the allylic bromide instead of chloride. If NBS cannot be used, Br2 might work, but you'll need to figure out the appropriate conditions. NCS might, in principle, work the same as NBS, but I think it's generally hard to do allylic chlorination because of the tendency to over-chlorinate. At any rate, great series of videos; they were a lot of fun to watch. Good luck!
Looking through an old 1979 organic chem book. Those are the best sometimes.
And there is a reference to isobutylene dimerization.
“In the presence of 60-65% sulfuric acid under mild conditions t-butyl alcohol undergoes dehydration to isobutylene, which is converted mainly to octylenes rather than higher polymers. “
2,4,4-trimethyl-1-pentene 20%
2,4,4-trimethyl-2-pentene 80%
In the experiment they say to reflux the t-butyl and sulfuric for 30 min. But maybe this is what was happening in your butylene drier ?
I don’t think this is what your final product was as they have boiling points of 101 and 104 respectively.
That was an amazing setup though. Hell for the cleanup. But awesome.
Roger Adams
John R. Johnson
Charles F. Wilcox Jr.
Laboratory Experiments in
Organic Chemistry
Seventh Edition
In case anyone want to look it up. There are quite a few good synthesis in there.
It goes on to say
Reactions generally involve the characteristic addition reactions of the carbon-carbon double bond with electrophilic reagents such as sulfuric acid, halogen acids, hypochlorous acid, chlorine, bromine, and oxidizing agents.
With unsymmetrical alkenes like propylene and isobutylene the mode of addition is highly selective. The electron-deficient fragment of the reagent adds to the carbon atom bearing the larger # of hydrogen atoms.
(Markovnikov rule) an exception to this rule is hbr to terminal alkenes in the presence of peroxides.
Substitution reactions of alkenes occur under special conditions at higher temps. Isobutylene reacts with chlorine at 500C to give methallyl chloride.
Daniel Coleman at 500C?? Aw man. Other references give cooling as needed... That's confusing. Hmmmmmm
Thats why most old organic chemists are bald. They pulled it all out. Lol
I love your show and that you are quite happy to show your failures rather than pretending it went perfectly every single time!
2:04 why not use a different liquid that's less dense than the product?
please try out the photochlorination of toluene in the gasphase, that would be a nice setup
So would #1 be the best route for the Chlorination of Methane??
Thanks! Just something I was wondering
Lol love that you had to dodge those HCl fumes.
Excelent my brother.
I don’t think you read comments in your old videos but alkenes react with concentrated sulfuric acid at room temperature to produce alkyl hydrogensulphates which can be boiled with water to form an alcohol.
what about letting it over Cl-ate and then use strong base to de-HCl-ate?
TM Fan that's... I mean..... That's a crazy enough idea that it might work???
Reaction not specific enough and requiring an energy level that is so high that you get side reactions, hmmmm sounds like you need to find a catalyst to help you.
Daniel Matthews no it needs an anti-catalyst, too many chlorine should are adding and I only want one! It needs to calm down somehow
That depends on the catalyst surely, some assist with specificity and allow for the desired reaction at lower temperatures. Such as 0C.
guild wars...?
Are you interested in a 250 mL heating mantle? i would donate it and send it to you.
thanks for the offer, but shipping stuff like that is expensive! And I only tend to give out my address to people I know well and all, but thanks for thinking of me!
Maybe you could start with formaldehyde? The structure seems similar
Mega bong freakout
Cleaning up all that glassware muse have been fun.
HV Lab ...honestly I've just dumped it all in a bucket and haven't got it it yet :(
maybe add some Na2SO3(aq) into the product collection flask to destroy excess Cl2 that made all their wae down?
TM Fan I was taking off the liquid at the bottom quite regularly, so it didn't spend much time in contact with the chlorine, even if some did make it down that far through the apparatus. But perhaps I should try to neutralize it away??
Ok thanks so I got another one: Haych-see-el
Rhodanide all H are now Haych from now on, by royal decree
Extractions&Ire 😍
Very ghetto apparatus. Love it
Where's your patreon?
Anthony Marks https://www.patreon.com/ExplosionsandFire
It's connected to my other YouTube chemistry account which is a different feel (if you haven't seen it before) so it supports the projects there, but ya I mean it is just me in the same lab in both channels :P
Extractions&Ire I didn't know if you had changed accounts or anything. I mean fulminating gold is soooo dangerous and all
Sulfuric acid strikes again
Could you not take a NMR at your University?
kalrbaum No unfortunately I'm not enrolled anymore, I graduated. I'm about to go back there soon but it's in a completely different area so I probably still won't have NMR access (unless I bribe some contacts nicely I guess)
How about bromination?
David Perhaps, but I feel it would be a lot less subtle, attacking the double bond a lot. Even if not, it would have to be dilute vapour phase, and generating bromine basically in situ like how I've been generating chlorine is much more of a problem.
If that made no sense, theoretically I think it's worse, and practically it's a bit of a nightmare, but I'll still consider it !
Extractions&Ire
That's my concern too, but maybe it's still worth a thougt
But whats the product you got? If it is 1,2-dichloro-2-methylpropane, I assume, you could convert it to 1-chloro-2-methylprop-2-ene by a Sn1 substitution with OH at the tertiary carbon and E2 elimination with conc. sulfuric acid.
Or you could react isobutene with bromine to intentionally brominate the double bond ant then follow the steps listed above to get it back🤔.
David I think he made 1,2,3 trichloroisobutane, boiling at 160 C and density of 1.3 so thats my guess.
These are beginner suggestions, but how about drying tubes to remove water? Slower addition of chlorine? Bubble isobutane through concentrated HCl? Liquefy, store, and test your isobutane separately to remove it as a variable, instead of managing 3 reactions simultaneously?
The best part of the video was when you removed the sulfuric acid trap, and immediately began producing results. That third of the system seems very well dialed in. A shite chemist would not have figured out to try that!
Also, what the hell was that red deposit in the sulfuric acid flask? It looked nice at night, but maybe it fluoresces yellow!
Could you demonstrate chlorination of paraffin wax?
Chlorinated paraffin wax has many uses. I would really like to see a demonstration of how it can be synthesised!
Awww man! :-(
I really don't know what could have gone wrong with that one.
If it is overchlorination, I guess going back to your first method with some acetate to scrub the HCl could possibly solve it, since the isobutene would then always be in excess until the very end. Assuming the scrubbing actually works.
I'm a little busy right now to really look into it and go back to the litterature. But I'll do some head scratching this week-end and get back to you! ^^
piranha031091 I know :( watching that liquid condense out as the two gases mixed, I was so confident.
And scrubbing out the HCl, is that the only thing that can add to the double bond? Or is the Cl2 gas reacting directly with it?
Sorry for replying a year later, but would an excess flow of isobutane be useful too? It looked like there was always an excess of chlorine gas. (Perhaps add an itty bitty flare at the end for style?)
make some nitroethane without a nitrite salt :p
TheRolemodel1337 haha aw why, can't people get nitrite salts?? And fairly sure there's already a video on YouTube with someone doing that... By decomposition of some other thing?
there are videos getting it from decomposing nitrate salts with for example calcium sulfite but the yields seem to be abyssimal and impure
also scaling up the reactions is not favorable since we're dealing with alot of molten nitrates
i can buy 0,5% NaNO2 mixed in NaCl for salting/pickeling meat but its kind of expensive and very time consuming to work up
George M. - 2019-11-16
The production quality screams "found footage from a chemist who was horribly killed by an experiment"