Making Metallocenes - Organometallic Sandwiches

Ғылым және технология

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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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Пікірлер: 112

  • @JacobTFuller
    @JacobTFuller Жыл бұрын

    Interesting but the audio is like a whisper, don't worry I'll still click like the button lol

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    Next time, Audio gain: +100 dB, got it 😎

  • @b3rnd

    @b3rnd

    Жыл бұрын

    @@Chemiolis I hadn't noticed at all. Seems good to me.

  • @covodex516

    @covodex516

    Жыл бұрын

    @@b3rnd you listening to everything on 90% volume? no he's right, it's simply to quiet.

  • @superme63

    @superme63

    Жыл бұрын

    @@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.

  • @tsirolucecomparison871

    @tsirolucecomparison871

    Жыл бұрын

    same

  • @user-de3mx9zj1p
    @user-de3mx9zj1p Жыл бұрын

    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!

  • @VinsCool
    @VinsCool Жыл бұрын

    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!

  • @deralchemist1990
    @deralchemist1990 Жыл бұрын

    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...

  • @douro20
    @douro20 Жыл бұрын

    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.

  • @That_Chemist
    @That_Chemist Жыл бұрын

    I'm glad to hear the sponsorship worked out for you :)

  • @Blakearmin
    @Blakearmin Жыл бұрын

    I'm into chemistry KZread but I haven't run across your channel yet. Subbed! This is a neat project. Keep up the good work!

  • @timecode37
    @timecode37 Жыл бұрын

    Love your style of videos! We appreciated the effort that goes into it

  • @durshurrikun150
    @durshurrikun150 Жыл бұрын

    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

  • @mattcarnevali
    @mattcarnevali Жыл бұрын

    Would love to see a revisit to this where you are able to purify the products. Would love to see more videos about organometallics!

  • @revenevan11

    @revenevan11

    Жыл бұрын

    Agreed, I want to see him demonstrate manganocene's thermochromic properties!

  • @WXUZT
    @WXUZT Жыл бұрын

    Really remarkable. So much resources have been invested. Thank You for your input and time !

  • @christosgiannoudis171
    @christosgiannoudis171 Жыл бұрын

    you are doing a great job...from an organic chemist somewhere in europe

  • @nilnull5457
    @nilnull5457 Жыл бұрын

    Excited for part 2 of this, with the cold finger in your possession.

  • @herwew7476
    @herwew7476 Жыл бұрын

    Great Video, love to see some more air free chem on youtube!

  • @yoyojoghurt123
    @yoyojoghurt123 Жыл бұрын

    Group 4b metallocenes are used for stereospecific synthesis of polymers!

  • @KTEX78
    @KTEX785 ай бұрын

    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

  • @kid_missive
    @kid_missive Жыл бұрын

    I remember this one from school. It's comforting to know that skilled people such as yourself sometimes have little accidents too!

  • @lablulz2483
    @lablulz2483 Жыл бұрын

    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!

  • @amkaktiv2886

    @amkaktiv2886

    Жыл бұрын

    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

  • @lablulz2483

    @lablulz2483

    Жыл бұрын

    @@amkaktiv2886 I was being conciliatory towards the OP's position for rhetorical reasons ;)

  • @durshurrikun150

    @durshurrikun150

    Жыл бұрын

    Chiral ferrocenes have been used for asymmetric catalysis or as chiral ligands.

  • @tracybowling1156
    @tracybowling1156 Жыл бұрын

    I definitely had fun watching you do chemistry!

  • @puo2123
    @puo2123 Жыл бұрын

    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.

  • @niconeuman
    @niconeuman Жыл бұрын

    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.

  • @bdnugget
    @bdnugget Жыл бұрын

    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

  • @arucane8635

    @arucane8635

    Жыл бұрын

    I thought metallocenes were cp5 ?

  • @G0ldunDrak0n

    @G0ldunDrak0n

    Жыл бұрын

    @@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.

  • @azxde9266
    @azxde9266 Жыл бұрын

    Congratulations on the sponser!

  • @thelox333
    @thelox333 Жыл бұрын

    Really like your videos!

  • @skeller90
    @skeller90 Жыл бұрын

    Excellent complex videos!

  • @rockybond42
    @rockybond42 Жыл бұрын

    i used metallocenes (specifically cobaltocene) in my undergrad lab for thin film Co3O4 synthesis! it shows potential as an electrocatalyst

  • @eier5472
    @eier5472 Жыл бұрын

    I admit these are better metal sandwiches than my peanutbutter & screws from the hardware store

  • @DerDrako
    @DerDrako Жыл бұрын

    Great work.

  • @davidli6931
    @davidli6931 Жыл бұрын

    Love seeing organometallic chemistry on KZread.

  • @Zenzicubic
    @Zenzicubic Жыл бұрын

    Lovely! I wish I could do this.

  • @xamadi199
    @xamadi199 Жыл бұрын

    No significant use? You might want to take a look at ziegler natta (kaminsky) catalysts. Nevertheless great video!

  • @G0ldunDrak0n

    @G0ldunDrak0n

    Жыл бұрын

    To be fair the catalytically relevant complexes are mostly "bent" metallocenes rather than the straight sandwich ones.

  • @victordonchenko4837

    @victordonchenko4837

    Жыл бұрын

    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?

  • @priyanshsuthar519
    @priyanshsuthar519 Жыл бұрын

    I can feel the pain you had when Cobaltocene got oxidised 😢

  • @jasondworkin6597
    @jasondworkin6597 Жыл бұрын

    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.

  • @gustavgnoettgen
    @gustavgnoettgen Жыл бұрын

    Wow, manganocene looks amazing

  • @tim21b
    @tim21b Жыл бұрын

    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

  • @jogandsp
    @jogandsp Жыл бұрын

    What do you mean they don't have any uses?? They have tons of uses, and half sandwich compounds are also super useful!

  • @johnykolk1414

    @johnykolk1414

    Жыл бұрын

    Can you list them?

  • @liambuchan4162

    @liambuchan4162

    Жыл бұрын

    @@johnykolk1414 good protecting groups for reactions, I guess? Like Zieglar-Natta polymerisation

  • @biggiecheese93
    @biggiecheese93 Жыл бұрын

    Nice video! Can i ask where you got the round bottom flask reaction block thingy at 1:56 from?

  • @xenoxaos1
    @xenoxaos1 Жыл бұрын

    If you need a cold finger.... My urologist has one... 🤣

  • @berukadehikari2634
    @berukadehikari2634 Жыл бұрын

    The solution of anhydrous cobalt (II) chloride is a nice deep blue color

  • @darkenblade986
    @darkenblade986 Жыл бұрын

    good stuff

  • @stamasd8500
    @stamasd8500 Жыл бұрын

    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.

  • @purplealice
    @purplealice Жыл бұрын

    So, back in the Metallocene Age, there were organic complexes held together with a metal atom...

  • @robertnichols2283
    @robertnichols2283 Жыл бұрын

    Cold finger- sounds like a 007 parody

  • @adrianhenle
    @adrianhenle Жыл бұрын

    You forgot the coolest example of metallocenes--double-deckers! I may be a little biased (my first-ever paper was on them)

  • @ericfortin5612
    @ericfortin5612 Жыл бұрын

    Hey i use the same heidolph hotplate at my work!

  • @ryanlucus1684
    @ryanlucus1684 Жыл бұрын

    Can they be used in tattoo inks?

  • @mastershooter64
    @mastershooter64 Жыл бұрын

    wow nice

  • @Seabed3434
    @Seabed3434 Жыл бұрын

    You should trymaking ruthanocene bis aza crown ether

  • @jhyland87
    @jhyland87 Жыл бұрын

    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

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    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

  • @hardiksavriya5325
    @hardiksavriya5325 Жыл бұрын

    Hello sir. Can you make video on synthesis of valerophenone.

  • @thepsychocybe7078
    @thepsychocybe7078 Жыл бұрын

    love me some metallocene chemistry

  • @nosmokingplz
    @nosmokingplz Жыл бұрын

    I almost remember the stench of the cyclopentadienes from my inorganic chem experimental class. Real puke maker.

  • @stephenjacks8196
    @stephenjacks8196 Жыл бұрын

    Simplest is Chromocene - DiBenzene Chromium. CrCl3 solution, add benzene and Zinc powder then stir.

  • @icebluscorpion
    @icebluscorpion Жыл бұрын

    Do one with cuper

  • @cvspvr
    @cvspvr Жыл бұрын

    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

  • @therandomchemist
    @therandomchemist Жыл бұрын

    Make Rhodocene, Its documented very well

  • @sbmatthew
    @sbmatthew Жыл бұрын

    Cool !

  • @FutureAIDev2015
    @FutureAIDev2015 Жыл бұрын

    What if you tried reacting ferrocene with fullerene? (Eve Online reference)

  • @seilgu
    @seilgu Жыл бұрын

    here we can't buy cyclopentadiene or its dimer, is there a way to make it ?

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    I don't think so, it's made with steam cracking of oil, it is odd that you can't find it.

  • @whatitmeans
    @whatitmeans Жыл бұрын

    Are there any metallocene like ferrocene but with a copper atom instead of iron?

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    There are derivatives, but I could’t find any simple copper metallocene

  • @Hiear
    @Hiear Жыл бұрын

    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.

  • @transkryption
    @transkryption Жыл бұрын

    enjoyable

  • @user-cf6yr3pd8m
    @user-cf6yr3pd8m Жыл бұрын

    Парень, ты нереально крутой, такие синтезы сложные дома снимать...

  • @lauvpatel497
    @lauvpatel497 Жыл бұрын

    what about olefin polymerization catalysts? while its old chemistry, metallocenes have been plenty useful.

  • @rylandsmith8552
    @rylandsmith8552 Жыл бұрын

    The video is very quiet compared to the typical KZread ad volume! I can hear it if I turn it up about 70% volume but then the ads startle me lol

  • @frausdolous8954
    @frausdolous89547 ай бұрын

    Metallic sodium is insane! use Na-H in oil. (OR CaH2) in oil.

  • @eier5472
    @eier5472 Жыл бұрын

    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?

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    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).

  • @sivasubramaniyanrangaraju4730
    @sivasubramaniyanrangaraju4730 Жыл бұрын

    *"Yes, I drink sandwiches."*

  • @user-yb5cn3np5q
    @user-yb5cn3np5q Жыл бұрын

    Is it really cyclopentadying in English? I always thought it to be cyclopentadiEne (-dee-an).

  • @karolus28
    @karolus28 Жыл бұрын

    cool

  • @skyethebi
    @skyethebi6 ай бұрын

    Uranocene when?

  • @robotnikkkk001
    @robotnikkkk001 Жыл бұрын

    =IT'S STILL SURPRISING ABOUT HOW FERROCENE IS STABLE,THOUGH ...............BECAUSE OF WE ALL SAW HOW FAST ALL THESE ARE GETTING DESTROYED,THOUGH

  • @karlbergen6826
    @karlbergen6826 Жыл бұрын

    An interesting video but the volume is weak.

  • @okboomer6201
    @okboomer6201 Жыл бұрын

    😭😭😭😭 air entered the flask. What a letdown.

  • @douro20
    @douro20Ай бұрын

    Every time I hear the term "gradient" it makes me nervous...

  • @Haemoglobuli
    @Haemoglobuli Жыл бұрын

    0:40 Oh my gosh, it always triggers me so much that they can´t draw the Lewis-Formula of Ferrocene correctly 😤

  • @feelincrispy7053
    @feelincrispy7053 Жыл бұрын

    You’re audio is too low dude. I can hear everything fine but I got my volume at max

  • @user-zx8oy2jf4d
    @user-zx8oy2jf4d Жыл бұрын

    lol at "useless ass bs"

  • @sergiokaminotanjo
    @sergiokaminotanjo Жыл бұрын

    Are these drugs? lf these arent drugs lm not interested

  • @alvinkwok587
    @alvinkwok587 Жыл бұрын

    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.

  • @Chemiolis

    @Chemiolis

    Жыл бұрын

    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.

  • @davidfetter

    @davidfetter

    Жыл бұрын

    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.

  • @alvinkwok587

    @alvinkwok587

    Жыл бұрын

    Yeah, I am sorry, but I just want to say presentation make or break a video.

  • @ivanovalle9764

    @ivanovalle9764

    Жыл бұрын

    @@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

  • @KeepAnimeDegenerate
    @KeepAnimeDegenerate Жыл бұрын

    Do you kn ow what cobaltocene converts to on exposure to air? My guess is cobsltocenium oxide, but i'm probably wrong.

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