Extractions&Ire - 2018-01-31
Did you know there's new Explosions&Fire videos? Check them out https://www.youtube.com/c/explosionsfire2 I outline an organic synthesis project that will involve 4 or 5 steps to turn tert-butanol into the chemical that is used to stop apples ripening. While it no doubt doesn't work indefinitely, this chemical is used worldwise to prolong the storage lifetime of apples to quite honestly extraordinary length. We live in a golden age of chemistry, ever since the 50s the developments have exploded to the extent that you don't even notice them. You do so many amazing things, nothing seems amazing. In my complete amateur opinion, Physics had its moment from 1850-1950, chemistry had its moment from 1950-2000 and now its the moment where biology gets to change the world. Anyway that doesn't have much to do with the video oops
Apples already last for years in storage so Im actually thinking pears or maybe even the pawpaw would be better for this since they are very sensitive and will ether rot or not in a much shorter time scale. but i'd be willing to give it a shot.
I'd love to hear some updates on this, from either Cody or E&F
Same
Did this end up happening?
@Ignyte I'm still watching through the series but looking at the videos I'm guessing he had a lot of trouble with chlorinating the isobutene and seems to either have given up or was waiting to get this hands on more reagents cause that's where it appears to stop.
Do they still spray alar before harvest?
Apples hate him. Find out how this man changed the apple industry by blowing up some with TATP
science_and_anonymous haha I did do that! Wow that was a while ago, good memory
Extractions&Ire Hahaha yeah, good times good times
I know shit all about Chemistry and I can’t stop binge watching his channel. Thanks YouTube
You should call it the Anti-Apple-Aging-Agent. There's a tongue twister for you, I'd like to see you say it in the next video. Plus alliteration is great.
I think you meant "Additionally, alliterations are also awesome"
When you're trying to tell someone about it, just yell at them. It's AAAA
I think you mean Apple-Anti-Aging-Agent.
Perfectly profound post, Eddie. 👍
@J.T I don't know, they might have been taking about an aging agents that also destroys apples.
Heh, dedicated... I was actually to lazy to click next.
7:56 -- If isobutene boils at -7°C, then you don't need dry ice. You can use water ice to which salt has been added; doing that can lower the temperature of the ice to as low as -21°C, which should be more than cold enough for your purposes.
Someone's made ice cream at home, i see? 🙂
@Dr. M. H. -- Yup, clever fellow :)
@Kevin Byrne yayyyyy i guessed right.
That, and it was my shy way of paying homage to your clever, low cost solution that didn't occur to me. Thx for the complement but you're much more clever than i, sir. 👏👏👏
In chemistry: first you get the apples, then you get the money, then you get the peaches.
OMG
That's sublime, Neo.
😂
There's no way you can ship an alkyllithium overseas. Even t-butyllithium is pyrophoric, so something with a cyclopropene in it... I'm surprised it doesn't spontaneously fall apart!
So yeah, that last part sounds like some seriously air-sensitive chemistry you're about to do. It takes some serious equipment (schlenk line, argon, proper fumehood, etc...) and some good training. Make sure you know what you're doing before you set yourself on fire with by making something that immediately burns by simple contact with air.
- edit - Actually, are you even sure about that step? Sounds much more likely to me that you'd be making LiCl, NH3, and your product. Otherwise, what happens of your chlorine?
I'd even expect dimerization to be quite an issue here, since alkyl chlorides with a superbase tend to make singlet carbenes (which should rapidly cyclopropanate with any nearby chloroisobutene)
firedrake rudy possibly... But I'd rather get a proper regulator, for this anyway. There'll be a lot going on with the reaction, the simpler I can make each part the better really
Argon is good. You might as well have a go at some inert atmosphere stuff because it's a very useful tool overall. I've got this 4-port, dual vacuum/gas manifold that I bought by accident a while ago. Don't know about shipping it to Oz though :)
Dual vacuum/gas line is best because you can do cycles of vacuum purge and inert refill to get rid of ALL the oxygen and water vapour. Then you can do the sensitive organometallic stuff (I was making pincer ligands for metallocenes).
Extractions&Ire wait, you said you needed "a super base". It might not solve the whole doing the actual reaction problem, but can't you use sodium amide or something else sodium based? According to my extensive research (5 minutes of googling and highschool chemistry knowledge) organosodium compounds are less reactive and not (as likely to be) pyrophoric.
@Explosions&Fire to heck with argon, just let it burn and upload it to the other channel. Pyrophoric you say?...would be a hit! :)
@2001Pieps That's not a bad idea, but organosodium compounds are a bit more reactive than organolithiums. Sodium is less electronegative than lithium so that the bond with carbon is even more tenuous. In some organic chemistry classes, you may hear that organolithium compounds are essentially Ionic, and this is not really true. It is however more true of organosodium and organopotassium compounds. I can't find if they are pyrpohoric, but I would wager they are and they do react with carbon dioxide in a pretty predictable way. Here is a bit of reading for anyone strolling through the comments http://myweb.liu.edu/~swatson/downloads-4/files/Chapter_15.pdf
I want access to this software....
Same
buy it. SciFinder or Reaxys
Having had apple growing grandparents: Yeah, fruits are only ripe once a year, dear city dwellers. So the apples are put in a large, cold, dark, climate-controlled room for the rest of the year. Which keeps them fresher for longer than you'd even remotely assume. That way you don’t have to buy expensive fruits from the other side of the world.
Nowadays, they clean them and then spray them with beeswax. That is antibacterial, and keeps the water in, and the crap out.
I don’t think 1-MCP is legal nor even necessary here in most of Europe.
Edit: More than a year old should not be! That’s a rip-off! Unless they got massive overcapacities for really bad seasons, and there actually was one, who’d buy an old apple when you can have a new one from this year?
People who don't know any better and live in the city. The apples I buy basically don't spoil, they can sit around for ages.
Just a small thing, we pick apples in mid autumn usually and right now, in mid february those same apples are in great shape still. Cooling and keeping it in the dark can do 4 months easily. It will probably stretch to 6
Secondly, you could buy a window air con. You can use it to drop the temperature of an antifreeze bath to neg 20C for an infinite time period practically. I assume it would be pretty easy to get a secondhand air con in Aus.
so this channel is run by an right arm now :p
The one methyl cyclopropene Looks like a cartoon drawing of a chemistry beaker.
That's reassuring you say biology now has a chance to change the world. I graduated in 2016 majoring in biology, and have yet to really apply my degree, but I am still hopeful.
Hey I’d love to get my hands on that software I wanna make borazine trinitrate
Hype!
I hope Cody will collaborate
Hey man that was fuckin great. I had to to take time off school cuz the wifes preggers so you n the other chem youtubers have been my chemistry fix. Keep up the awesomeness bro.
Nice video on a possible route.
I wonder how many viewer understand the hours and hours spent researching a project like this? I really appreciate you showing and explaining the ideas you've come up with for this complex synthesis. Cheers
We have about 4000t of ethylene at work.
We crack it from ethane then send it to be polymerized.
But every few months BOC buy a truckload that ends up going to supermarkets for ripening fruit.
You're giving me flashbacks to senior design in ChemEng, designing and costing an ethylene cracking plant... Down the number of bricks in the chimney. 😣
Nice project! Anyone call Cody
lol
What University are you in...and which subject you are studying about??its obvious though but syill
SciFinder is the bestt
Unlimited source of citations lol
It's at minimum one year at maximum 2 years
Your diagram looks like 2-methylcyclopropene. You're sure you know what you're doing?
Also, to make 1-methylcyclopropene, it seems you need to start from 3-chloroisobutene, rather than the 1-chloro you've drawn there. Seems like strange thing to result from the chlorination anyway though. Under a radical mechanism I'd expect the allylic carbon to be substituted so you're probably fine with that route.
Also the lithiation of the cyclopropene looks like an erroneous assumption. Perhaps you ought to consider LDA as a preliminary synthetic target?
AguaFluorida I think the lithiation of the cyclopropene was incorrect, or at least to assume that 'hey this is a stable spot to stop' is completely incorrect, yeah
AguaFluorida ahhhhh I can't believe this, I drew the structure of the chlorine in the wrong place. I had a very simple task for this video, all I had to do is get the structures correct, but it seems I've not managed to do that.
The chlorine should be on the saturated carbon, so be the 3-chloro not the 1-chloro. I'm disappointed I've cocked it all up.
Yep. Methallyl chloride is what you want. But, hey, it's easier to make than the intermediate you've shown! Also lachrymatory as fuck, of course :'/ http://www.gelest.com/wp-content/uploads/ENEM2040_METHALLYL-CHLORIDE-tech-95_GHS-US_English-US.pdf
Extractions&Ire
Yeah, i was looking at it sideways and wishing you showed the electron pushing cuse something didn't quite add up :P
What is that software?
You mean Reaxys? As mentioned, it allows to draw a structure and to search for its synthesis (if it is reported in any paper). However, it's a commercial database and can be only accessed by subscribers (many chemistry-related universities provide access for their students and scientific employees).
Nice. Classic 3-exo-tet there after lithiation.
What were the 2 programs?
Ethylene from bananas also created some superstitions around bringing bananas on boats, usually when it rotted the apples onboard
Hi
Fruits are like apples products, already year old technology when they are sold
Cody catalysis :)
The Gayest Person on YouTube how's the exotic thermite series doing?
I’d love to know where you got the t-butanol! I couldn’t find any recently and last time I got some I could only get 30mls from the USA. Unfortunately they no longer have any. This should be interesting and a unique idea.
AllChemystery I originally got mine from the US a few years ago too! Was expensive for the amount, but didn't need much for the K production reaction yeah.
Was an independent lab store (not a chain) so I can't help you yeah, I was very surprised I found it! Could send you some if you need it, probably not going to use it all in this synthesis (or perhaps none at all!)
Extractions&Ire only if that’s not a problem. Do this first though to see how much you use of course. At what scale will you be attempting this synthesis? Not too large I would think. Dry ice could be costly. 8.80 a kg at BOC ( I got some two days ago) but you will probably use several kg since you won’t be able to do it all in one day. Hopefully you can pull it off! It would be a pretty epic effort.
NH2- is pretty nucleophillic. Are you sure that would perform dehydrochlorination and make 2-Li-1-MCP and not just kick off chloride to form isobutenylamine?
Any updates?
Next video:How to make humans immortal through chemistry
Some varieties of apple keep six months... Depends on the variety. Would be interesting to know the internals on those varieties... Low or no ethaline?
Make a time capsule and put the apple inside
So. Cool! Now I gotta see if Cody’s lab took the bait!
Yo speaking of superbases I've been thinking of an interesting sodium alkoxide synth for a while now... Electrolysis of salt over Hg(0) electrode --> drain the electrolyte --> wash the surface of the mercury electrode with MeOH --> Cover the DIY sodium amalgam with iPrOH (or whatever, IPA is the best OTC alcohol for this imo) under N2 --> Sodium isopropoxide pKa ~28... I'm too cheap to buy mercury, pls try so I can observe and record
Does it work for bananas too?
No
How are you going to store the isobutene? Maybe you can store it in the freezer with the lowest temp possible.
Maybe dcm can be used for the chlorination solvent.
Isn't CaC2 a super Base?
I'm going to have to use the isobutene pretty much after I make it, hopefully ill have enough glassware that I can just kinda, switch from one setup to another.
Perhaps, that would be useful, and probably better than toluene.
Not sure if CaC2 is a superbase, I've never heard that before. Surely it's insoluble anyway right? I'll look it up
Extractions&Ire the calcium carbide page on the sciencemadness wiki mentions that calcium carbide is a super base. Not sure if it's accurate though. Do you have a source of DCM? I can buy 100 ml or 450 ml bottles for a equivalent of a few Australian dollars. It should be more inert to chlorine than toluene.
I reckon the apple is about a year old
Did cody ever finish this off?
Naw if you read some other comments you'll see he never even tries. The lithium compound is pyrophoric, and a bunch of other reasons. It's a bit out of his current capabilities
Aw yeah I guessed 1 year
Mowskii you are good
1 year ago.
ethene
Hi I'm from Italy and I completely agree with you, this will be the biology century, and is one of the reason why I decided to study Biology at university, now I'm at the 2nd year of five.
Nice video, keep on doing what you do, yours and other american chemistry channels are my favourite, even if they aren't in my language so sorry if you don't understand what I mean but i tried ahah
Lele Secchi Biology is a good choice to study, well done! Thanks for watching and commenting :)
Me like it
Wouldn't calling it 1-methylcycloprop-1-ene make more sense, so we know where the methyl group is relative to the double bond?
That's a part of IPUAC nomenclature. If something has only one double/triple bond, it's always considered the "main" part of the molecule, so everything else is relative to it. Same with cycles in molecules - cycles are usually also prioritised, and here we have both, so you get cyclopropene. And then you count carbons from start to end, and with double bonds you start with the atom closest to the double bond, so here it doesn't matter which of the two carbons with double-bons will be first, it will be one of them and he will have the methyl, if you say it's on 1. Similarly, if you want to say that a carbon with no double bonds has the methyl you just say 3-methyl, and, once again, you can't get confused. I don't even know what's the correct name of the thing he wrote down, I have 0 clue what it should be called
Extractions&Ire - 2018-02-01
Honestly I can't believe that I've gone this whole video drawing the double bond in the wrong place. I draw 2-methyl cyclopropene, not 1-methyl cyclopropene. The double bond should be 1 carbon over. Way to ruin my credibility.
Everything in the video I say is still correct, just on the day of filming I drew up the thing wrong on the board. Oh :(
blabla62871 - 2020-03-31
how exactly is called that software for the reaction design? thank you!
Woodywoodmc - 2020-05-05
Reeeeeeeeeeeeeeeeeeeeeee
James Tranos - 2020-08-04
blabla62871 chem draw
Kyle Pedretty - 2020-09-16
AguaFluorida i came here with concerns. seems you handled it 😆
Kyle Pedretty - 2020-09-16
James Tranos no, he’s asking for SciFinder or Reaxys