Making Metallocenes - Organometallic Sandwiches
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- čas přidán 10. 07. 2022
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In this video I am doing syntheses to make Ferrocene, Stannocene, Cobaltocene and Manganocene. Ferrocene and Stannocene are relatively simple to produce, but both cobaltocene and manganocene are air-sensitive. This is why these compounds are much more challenging to make. Especially when hot, these compounds will degrade extremely fast in air.
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Interesting but the audio is like a whisper, don't worry I'll still click like the button lol
Next time, Audio gain: +100 dB, got it 😎
@@Chemiolis I hadn't noticed at all. Seems good to me.
@@b3rnd you listening to everything on 90% volume?
no he's right, it's simply to quiet.
@@Chemiolis I've got some pretty bad factory deafness, and have no problem saying that your audio is fine. At 33ish%, it is perfectly audible, providing there are no other sounds to interfere. With light background noise, 50% is sufficient.
same
Seeing university chemistry on youtube is really interesting. Never expected to see these out of my lab, out here. Best thing about you being you're not following any trend(like most chemistry youtubers out here :) ) , rather you're showing what actual chemistry looks like. Keep it up mate!
The ending was heartbreaking, the reaction (no pun intended) to the failure made me laugh, but I feel sorry for the loss!
The air sensitivity was not an exaggeration!
Hi there, atomic physicist here... I can report that Metallocenes are quite interesting for us because they provide a good way of transfering metals via the gas phase at room temperature or below. I recently conducted an experiment at a so called 'electron beam ion trap' EBIT where metal atoms are placed into an electron beam to rip off electrons and trap the resulting positively charged ions in the negative electron beam's field. Afterwards you can study the interaction of ions and electrons in a well defined and spacially confined area. A very nice way of getting the metal atoms into the crygenic EBIT is by using a Metallocenes - like Ferrorcene in our case - because you can just hook up a gas cylinder and use a simple gas inlet-valve. Hope that's at least midly interesting...
I'm glad to hear the sponsorship worked out for you :)
Ferrocene has some promise as a gasoline additive. It is already sold as an antiknock compound to allow modern gasoline to burn better in vintage car engines. It does have the unfortunate side effect of leaving iron deposits on spark plugs, especially in an engine that runs a bit rich. It is also effective at reducing smoke and sulfur trioxide emissions from burning coal, even in small amounts.
Love your style of videos! We appreciated the effort that goes into it
I'm into chemistry CZcams but I haven't run across your channel yet. Subbed! This is a neat project. Keep up the good work!
It's much easier to learn from a real practical synthesis than from qa book wher you only can only see the drawed reaction theoretically. Thank you very much for the video
Diphenylfosfinoferrocene is used as a lygand in palladium catalysed couplings, some chiral metallocenes have been used in asymmetric catalysis and some are used as standards in organic electrochemistry
you are doing a great job...from an organic chemist somewhere in europe
Great Video, love to see some more air free chem on youtube!
Really remarkable. So much resources have been invested. Thank You for your input and time !
Would love to see a revisit to this where you are able to purify the products. Would love to see more videos about organometallics!
Agreed, I want to see him demonstrate manganocene's thermochromic properties!
I remember this one from school. It's comforting to know that skilled people such as yourself sometimes have little accidents too!
Excited for part 2 of this, with the cold finger in your possession.
nice work, I'm glad I found your channel! To be fair to metallocenes, they might not have found many practical applications, but they were very important in developing our understanding of chemical bonding. At the time the structure of ferrocene was first correctly described, it was so unusual that the journal editor accused the future nobel laureates of being high on hashish!
Not many practical applications? Like planar chiral catalysts, photo physical activ complexes, metallocene polymerisation, THE innert observing ligand in metallorganic catalysis/reactions, ... Sorry bro :D
@@amkaktiv2886 I was being conciliatory towards the OP's position for rhetorical reasons ;)
Chiral ferrocenes have been used for asymmetric catalysis or as chiral ligands.
I definitely had fun watching you do chemistry!
Group 4b metallocenes are used for stereospecific synthesis of polymers!
Very nice video! Metallocenes are awesome. I may have to make ferrocenium hexafluorophosphate soon, starting from ferrocene (which is the only cheap one). I would love to try cobaltocene sometime! I will definitely rewatch your video before that.
Iron half sandwich complexes are used to stabilize cyclobutadien.
You can make NaCp by reacting dicyclopentadien with sodium. The product can be washed with hexane and should be white.
Congratulations on the sponser!
I've cracked my fair share of Cp2 and I am surprized you didn't comment on the smell, you must have a super good fume hood lmao. It used to fill my lab with this lovely super dense gasoline smell
I thought metallocenes were cp5 ?
@@arucane8635 Cp2 is just the product of 2 cyclopentadienes reacting via Diels-Alder: dicyclopentadiene. Metallocenes are Cp2M where Cp is the cyclopentadienyl anion/ligand (C5H5) and M is an oxidation level +2 metal like Fe or Co. I'm not familiar with any compound denoted "Cp5". There is a CpMe5 though, which is permethylated (or pentamethylated) cyclopentadienyl. Then there is Cp2MX and Cp2MX2 with X being another anionic ligand, like chloride, and M a metal at oxidation level +3 or +4 like Ti or Zr.
i used metallocenes (specifically cobaltocene) in my undergrad lab for thin film Co3O4 synthesis! it shows potential as an electrocatalyst
Excellent complex videos!
Really like your videos!
Love seeing organometallic chemistry on CZcams.
No significant use? You might want to take a look at ziegler natta (kaminsky) catalysts. Nevertheless great video!
To be fair the catalytically relevant complexes are mostly "bent" metallocenes rather than the straight sandwich ones.
I have heard of Ziegler-Natta catalysts but apparently most industrial production of polymers uses other methods (like I assume free-radical polymerization?). What is the use that Ziegler-Natta catalysts find then? I know that Ziegler-Natta catalysts can produce polymers with regular tacticity, but what is the purpose of this?
Takes me back. I once tried, and perhaps partially succeeded, in making ferrocenylnickelocene (cp-Fe-cp-Ni-cp). But I was unable to purify it to be sure. Maybe you can do better.
I admit these are better metal sandwiches than my peanutbutter & screws from the hardware store
I can feel the pain you had when Cobaltocene got oxidised 😢
Great work.
Wow, manganocene looks amazing
The videos are great but why is the sound so low? I have to increase my volume to 2 or 3 times my normal to barely be able to hear anything
Lovely! I wish I could do this.
If you need a cold finger.... My urologist has one... 🤣
Nice video! Can i ask where you got the round bottom flask reaction block thingy at 1:56 from?
The solution of anhydrous cobalt (II) chloride is a nice deep blue color
Can they be used in tattoo inks?
What do you mean they don't have any uses?? They have tons of uses, and half sandwich compounds are also super useful!
Can you list them?
@@johnykolk1414 good protecting groups for reactions, I guess? Like Zieglar-Natta polymerisation
You should trymaking ruthanocene bis aza crown ether
Cold finger- sounds like a 007 parody
You forgot the coolest example of metallocenes--double-deckers! I may be a little biased (my first-ever paper was on them)
Hello sir. Can you make video on synthesis of valerophenone.
Ferrocene has actually been evaluated in the past as an antiknock agent in gasoline to replace tetraethyl lead. It works, but then other better compounds (like methylcyclopentadienyl manganese tricarbonyl, another metallocene) came along and ferrocene didn't make it to being used for this purpose industrially.
Hey i use the same heidolph hotplate at my work!
good stuff
Simplest is Chromocene - DiBenzene Chromium. CrCl3 solution, add benzene and Zinc powder then stir.
1:51 what's that metal thing you use to xfer heat from your hotplate to the rbf called? I could definitely use one of those
They are called Drysyn from Asynt, there is also heat-on block from Heidolph which is basically the same, probably others have similar products as well
wow nice
man, this reaction is full of precursors that don't want to sit still. cyclopentadiene wants to wants to dimerise, iron ii chloride wants to oxidise, and potassium hydroxide wants to absorb water from the air
So, back in the Metallocene Age, there were organic complexes held together with a metal atom...
I almost remember the stench of the cyclopentadienes from my inorganic chem experimental class. Real puke maker.
love me some metallocene chemistry
what about olefin polymerization catalysts? while its old chemistry, metallocenes have been plenty useful.
here we can't buy cyclopentadiene or its dimer, is there a way to make it ?
I don't think so, it's made with steam cracking of oil, it is odd that you can't find it.
Make Rhodocene, Its documented very well
Парень, ты нереально крутой, такие синтезы сложные дома снимать...
Are there any metallocene like ferrocene but with a copper atom instead of iron?
There are derivatives, but I could’t find any simple copper metallocene
Cool !
*"Yes, I drink sandwiches."*
enjoyable
What if you tried reacting ferrocene with fullerene? (Eve Online reference)
Do one with cuper
How can you say that metallocenes are useless? This group of compounds is used as catalyst in ethylene or propylene polimeryzation to form various type of poly(ethylene) and poly(propylene) with such a controlled manner, that was never possible in history. Those PEs are so called mPEs (metallocene poly(ethylenes)) and are used in many, many aplications - from laminates, where PE is required to be as transparent as possible, to big plastic bags that are used as vacuum bags and their heat seals need to be tight as much as it can to prevent air leaking inside or on the other end of spectrum - small bags, f.e. chips bags, that are mass produced in high speed process, where the seal need to be formed really fast and has to hold air inside the bag. Those are just some of the applications of those PEs, like I said, there are many more, and all of that is possible thanks to metallocene catalysts.
The video is very quiet compared to the typical CZcams ad volume! I can hear it if I turn it up about 70% volume but then the ads startle me lol
Metallic sodium is insane! use Na-H in oil. (OR CaH2) in oil.
Also, since you live in the EU, how do you deal with EU regulations? And how are the regulations regarding buying chemicals in the Netherlands?
If you set up a company then regulations that hold for private persons no longer apply and you can buy chemicals that normally would be restricted. Of course you still have to provide information. Sometimes a simple declaration form, and sometimes your passport information or your chemistry degree (proof of expertise).
Is it really cyclopentadying in English? I always thought it to be cyclopentadiEne (-dee-an).
Uranocene when?
cool
An interesting video but the volume is weak.
=IT'S STILL SURPRISING ABOUT HOW FERROCENE IS STABLE,THOUGH
...............BECAUSE OF WE ALL SAW HOW FAST ALL THESE ARE GETTING DESTROYED,THOUGH
😭😭😭😭 air entered the flask. What a letdown.
0:40 Oh my gosh, it always triggers me so much that they can´t draw the Lewis-Formula of Ferrocene correctly 😤
Every time I hear the term "gradient" it makes me nervous...
You’re audio is too low dude. I can hear everything fine but I got my volume at max
lol at "useless ass bs"
Are these drugs? lf these arent drugs lm not interested
Your video is quite good, the only thing is the presentation need some work, the voice should be... well. Take a look at Nilered video, I guess you will find some inspiration.
NileRed has like a decade of experience with voice overs, It’s really challenging to do, especially when not naturally being blessed with an amazing speaking voice. If you go to NileRed’s earliest videos he doesn’t talk like he does now. I can’t simply match the way he speaks today, such things require years of experience.
I'm sure you meant well, but telling somebody to magic up a giant budget, a crew, and over a decade's worth of experience is NOT that. I suggest you apologize.
Yeah, I am sorry, but I just want to say presentation make or break a video.
@@Chemiolis I Think your channel is better for educational purposes , I don’t mind the voice at all. You explain everything really well to the point and you don’t need to Mimic NileRed. Both him and Cody’s lab while they are both good in their own distinct ways , they are more about showing cool chemistry conversions to gain clicks (which is okay) but your synthesis videos are a more complete learning experience while still providing some of the cooler stuff
Do you kn ow what cobaltocene converts to on exposure to air? My guess is cobsltocenium oxide, but i'm probably wrong.