> chemistry > organiques-simples > succinimide-from-succinic-acid-extractions-ire

Succinimide from Succinic acid

Extractions&Ire - 2020-04-11

We do a ring closing reaction to form a needed organic building block, as usual sacrificing some glassware and sanity in order to get it done. Also, I paint. As somehow requested. 
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Music: from Aphex Twin's soundcloud dump, track name:
1- Dance And Play
2- 14 07 B
3- lost track[dat 24]icbyd

Extractions&Ire - 2020-04-11

the fact that I go this whole video without making one SUCC joke is honestly a tragedy

De paus van de Lilith Kerk - 2020-06-28

I first didn't missed a "succ joke", now I have read your comment I kind of feel "robbed", .....ah well, I still enjoyed the video even without a succ joke 👍

Zerron Kaibo - 2020-08-17

Succs that it nearly went yellow

Bayvel - 2020-08-27

What is the matter with you, you beautiful bastard

Antimatter Lord - 2020-11-23

I was thinking that exact same thing. I was waiting for the meme man face to appear during the video.

Alan Wesson - 2020-12-16

At least you said dilute heat.

NG - 2020-04-11

Don’t you dare clean anything. The whole “trailer park meth lab” look is part of the charm of the channel.

Danielle Spargo - 2020-04-11

it's his aesthetic lol

Amipotsophspond - 2020-04-18

Alexander Fleming discovered penicillin by hording used petri dish to the point flies got stuck died on them and started to mold. Lea & Perrins forgot about Worestershire Sauce under some stairs after a few months they thought the longer fermenting time tasted good(WTF they tried it). just saying some good things have come from the slovenly.

Harold Saxon - 2020-05-02

@Extractions&Ire hopefully this brings you a little less yellow in your life

bromiso valum - 2021-03-09

@Extractions&Ire A clean lab = an insecure chemist ;^)

bromiso valum - 2021-03-09

@Amipotsophspond Worcestersauce is basically rotten anjovis, but rotten in salt. Romans did the same, they called it garum, you let salted fish guts/heads rot until it is completely liquified. Still exists in Italy under a different name, and like you said, in England.

Rhodanide - 2020-04-11

Tom: "Ammonia is my least favorite gas to deal with"

Me: nervously glances over at Hydrazoic acid

Dragon Slayer Ornstein - 2020-04-13

@Californium-252 don't forget extremely RADIOACTIVE! RADIOACTIVE!

Californium-252 - 2020-04-13

@Dragon Slayer Ornstein That's fluorine 18.
Fluorine 19 is not radioactive.

Dylan Capper - 2020-04-13

@Californium-252 after fluorine turned 21 it settled down

Californium-252 - 2020-04-13

@Dylan Capper A joke about the US' minimum age requirement for drinking? It seems like it.

bromiso valum - 2021-03-09

Diazomethane always sounded sexy to me, sexy in the "stay the fuck away/I wish but no don't even contemplate" kind of way. And ketene of course, another kinky nono.

Dylan Russell - 2020-04-11

Tom: don’t request videos of me painting

Also Tom: Lofi hip hop beats to relax/paint benches to

Marcus Langeström - 2020-04-11

"It looks red on camera" no, it looks yellow. And we all know what that means.

James Trotman - 2020-04-12

I've no idea what it means xD

Marcus Langeström - 2020-04-12

@James Trotman Yellow is his kryptonite. If any experiment turns yellow, it's down hill from that point on 😋

Eph-Jay Music - 2020-04-13

🤣🤣🤣

Juuul - 2020-04-15

That he may be colorblind and not realize it?

Marcus Langeström - 2020-04-15

@Juuul That could be it!

Klaudio - 2020-04-11

The only crack shack used for actual chemistry <3

go away - 2020-04-11

I guarantee you there are many more crack shacks that are used for actual chemistry!

ImBadAtGames - 2020-04-14

The only crack shack used for *LEGAL chemistry. Don't be dissing the meth cooks out there

Felixkeeg - 2020-04-11

"Should've sanded it all back, everbody's going to say that"
Yes, you should've'd

Extractions&Ire - 2020-04-11

The YouTube audience is basically my conscience, who I often chose to ignore

Puchałke - 2020-04-12

@Extractions&Ire and then paint it white with organics rich paint ;)

ABadImagination - 2020-04-18

if ya gonna go back n sand it, you might as well bog n re-sand for a mint finish

ReactiveChem - 2020-04-11

That 6% recovery from subliming onto an rb flask hurt a little

Extractions&Ire - 2020-04-11

I felt it in my bones

Tom Lynx - 2020-04-16

@Extractions&Ire I think that's actually from the various fumes you produce in the shed :)

No no - 2020-04-11

Hey congratulations on the clean bench!

Oh and congrats on the chemistry thing, whatever that was.

Extractions&Ire - 2020-04-11

It really felt like an achievement honestly

Pvt_Crunch - 2020-04-11

You should re-title this video to "Finally Painting the Desk".

Extractions&Ire - 2020-04-11

That's really the main content, painting with a little bit of chemistry

Rando Jenkins - 2020-04-11

I came to say this :D

Helix Relics Show - 2020-09-07

@Rando Jenkins funny

Jonas Gilch - 2020-04-11

I am studying chemistry in Germany. Every time it SUCCs I watch one of your videos and motivation is back. Thanks a lot for those boosts.

Extractions&Ire - 2020-04-11

Glad I can help, good luck with it all, I believe in you!

JamesG - 2020-04-11

Don't believe it, Jonas! He said that to me -- now I have no friends and all my glassware is stained YELLOW.

Jonas Gilch - 2020-04-11

I am more afraid of the yellow stuff than having no friends to be honest. Last semester a had some nerve racking time with synthesising some yellow GaCp*. That is enough for quite some time.

Boring Old White Guy - 2020-04-11

Have you considered that the trouble you have in determining the ph is due to your use of YELLOW yest strips?

R. Mishra - 2020-09-10

This

bgdwiepp - 2020-04-12

i love your approach of doing real chemistry badly, it has a certain type of charm, very much like your approach of doing real painting badly.

THECREATOR1099 - 2020-04-12

Get an electric sander will make your life way easier whenever you want to re do the tables

Ben Holcombe - 2020-04-11

I think you should go bromination with Tet. Should be highly efficient, and succinimide not soluble in Tet.

The n chlorosucc is less selective for allylic position and seems experimentally more difficult to achieve

Extractions&Ire - 2020-04-11

Ok, noted. More effort, but if it actually works, it's a much better option

Mason Cook - 2020-04-12

I agree, the chlorosucc is going to be more wild than the bromo, my lab does bromosucc in dcm when we need to do additions like these. Good luck on the process, lots of charm in your meth lab

GoldenChilder Pocklurt - 2020-04-12

No it’d have to chlorinate at the allylic position, there is no choice, surely. NCS in ch2cl2 should be fine. Either way purification could be easy by adding a little petrol to crash out succinamide and filtering, followed by distillation

Plebestrian - 2020-04-11

if it's yellow and it works, it's actually orange™

Random Experiments Int. - Experiments and syntheses - 2020-04-11

I always like the random off-topic parts of these videos :D It feels like a little break between the chemistry parts. Nice synthesis! I'd recommend to always put some coolant like ice and water into the flask, which is used to resublime a product. This could increase the yield.

Mehmet Soylu - 2020-04-11

"It's going yellow"
Me: Nervousness intensifies

Christian - 2020-04-11

Nice, that you finally painted the desk. I think a second layer might be a good idea, though. And probably with the enamel you were talking about. Hope to see that in an upcoming video!

Sebastian Flynn - 2020-04-12

I demand either a video or a live stream dedicated to painting the table.

appLez - 2020-04-11

Loved the video, thank you for this Easter special :)
Bloody yellow chemistry haha

2001Pieps - 2020-04-11

Maybe you should have stripped off the old paint. If only you had some sort of agent to do than with...

CRM-114 - 2020-04-11

Stripping paint is a waste of good DCM 😅

Hobo Sullivan - 2020-04-18

Yeah. I know for a fact he's still got those ampoules of bromine.

2001Pieps - 2020-04-18

@Hobo Sullivan Yeah, maybe just bleach the table.

Kevin Bauer - 2020-07-04

A nice thick coat of "touch powder" would take care of the old paint, and give you a rich brown finish.

{} - 2020-11-19

@Kevin Bauer that's like advertising death

Nikolas Hadjipaschalis - 2020-04-11

NH3 is my least favourite gas to deal with
SO2, H2S, HCN: are we a joke to you?

go away - 2020-04-11

Accidentally generated SiH4 almost set my kitchen on fire once.

Peter Schluss-mit-Lustig - 2020-04-12

F2?

PuO 2 - 2020-04-12

@Gowrav M i nearly did that on christmas eve while trying to make elemental mercury xD I was getting huge amounts of H2S when i reacted a mixture of NaOH, S and HgS with Al.

GRBTutorials - 2020-04-12

COCl2: The previous ones are nothing to me!

Luis P. - 2020-04-19

@GRBTutorials It doesn't set everything it touches on fire, like F2 does, while also killing you at any sort of exposure that isn't fire because of the HF that is produced in contact with moisture. SiH4 explodes on contact with air. Phosgene is probably the most painful way to die out of all of those, though.

Luhsteesay _ - 2020-04-11

I know little to nothing about chemistry but still enjoy the videos fam, love your stuff!

MintGarnish - 2020-04-11

Next step: paint the benches with chalk paint to give you more room.

Also O O F on the 6% 😂

MrPinknumber - 2020-04-11

Ahhh yeah, that cleaning is so satisfying to watch. Good job !

Keith Lange - 2020-04-11

Thank you so much for these uploads, m8. It's really helping us get through lab withdraw during quarantine ;___;

Tom Lynx - 2020-04-16

The part where you painted the bench and the whole screen became white and clean purified my soul Tom.

Parker Psillides - 2020-04-17

The creator of this channel is interesting, kinda reminds me of myself, the way in the beginning we see a more subdued but unorthodox experiment which fails but really the guy knows what he’s doing and goes absolutely ham on the second experiment like a real mad scientist

Glorious Meme - 2020-04-11

Hey! Ive binged your entire channel. Love the chemistry and keep up the good work!

Extractions&Ire - 2020-04-12

Glad you like the vids mate!

Thrustmaster64 - 2020-04-12

Thank you for the nice paint footage! :)

Litespark - 2020-04-13

Finally a new video!
You're one of those channels to me that i actually drop everything else when i see they uploaded.

Snørgel - 2020-04-11

"If you watch this Channel for a wile, you might know that i am not good at cleaning and keeping promises"




Hmmm...

Kold Fizzion - 2020-06-17

Yea!! More awesome chemistry videos please.

TheBackyardChemist - 2020-04-11

For real longevity, you need to paint that bench with 2 part epoxy paint/coating.

William A. - 2021-03-03

that's why I hate organic chemistry. yields... once I made a reaction that I had 2.65% yield, never felt so wasted, humiliated and enraged at the same time!

Aiden Allweiss - 2020-04-11

Watching you paint that unstripped, unsanded bench hurt a little.

TrojanCommander - 2020-04-21

Thank you for giving me the idea of making Benzine from PET. Three years after watching that video, my graduation project is about designing a reactor for that exact reaction.
I changed my major from accounting to Chemical Engineering because of you and nilered. I'll hopefully graduate before the world ends. :D

Extractions&Ire - 2020-04-21

That's super cool!! And if you have any outcomes from that project, please let me know, especially if there's a writeup about it. It was a very interesting project that I did not get very far with, so would be really interested to see how you improve the method and give it another go! I sometimes miss comments, so feel free to DM me on Twitter too if I don't respond, good luck mate!

Nathan Klaft - 2020-04-11

Man a NileBlue video yesterday
Extractions&Ire today!
I really enjoyed the explanation of the ring closing reaction
Also that's really good way to half neutralize, I'd always just try to measure 1/2m base per 1m acid, Its kind of finnicky with a bad scale

Lukas Wursthorn - 2020-04-12

Generally, the bromine substituted isobutene will react much more readily than its chlorine substituted brother. It will, however, also degrade faster.
What are your reaction conditions of the ring closure reaction? If it is a low temperature reaction, you might be better off using the bromine derivative. Also, bromination using NBS will probably be easier than chlorination using NCS. I would therefore suggest going the bromide route, even though getting the actual NBS is harder. I think it will be worth the effort.

R Johnson - 2020-04-11

Great to see another one of your videos!

William wedgwood - 2020-09-21

"at least I don't have to clean it"- you should sell shirts

Hard Rock Lobster Roll - 2020-08-11

I like your neutralization and reacidifcation technique because it involves little to no math

Ryan Phillips - 2020-08-25

Make more videos bruh, I’m tryna get through quarantine by watching quality content

Truly Infamous - 2020-04-14

I honestly love the lab set up compared between you and Nilered. Yours is so relatable. Although I only have about 7 or so basic pool and house chemicals, I do have a lot of pool chlorine. I've quickly learned that chlorine only smells like a pool in low concentrations. It smells like pain when you breathe in more.

Drakkar Calethiel - 2020-04-11

Aw yes! Back on track for the 1-MCP synth!

Extractions&Ire - 2020-04-11

We will get there!!

Deliläs - 2020-04-11

ideally you want to remove the old paint

Will Ford - 2020-04-14

You’re finally returning to the 1-MCP experiment!

Anders Moore - 2020-04-12

Wow, you actually did it. You absolute mad lad!

À fond les ballons - 2020-04-12

Very nice! I was happy to see an ammonia + acid condensation and not the super classic urea version.
I made acetamide this way and had the same yield problem, then I found the trick: The best way to do it is to mix the acid + ammonia in the distillation flask and distil directly the water out and then the product.
Don't evaporate in a beaker, these amides tends to evaporate very easily with water, don't consider your just removing a solvent, the vapor is always a mixture.
That's a very good idea to go on N-chlorosuccinimide for that chlorination, it usually works on chlorinating allylic position. I wish you luck on that one :) You may however have to figure out how to react the gas with the NCS without having the NCS in excess...

Mike Master - 2020-04-12

Great comment!! I'm curious what you would think about generating ammonia gas and bubbling it into the acid and solvent, and if there would be any solvent you knew of that would be easier to work with than water?

À fond les ballons - 2020-04-13

@Mike Master Thanks :)
That would certainly work and I think the best solvent would be a polar one (in theory) to dissolve both the ammonia gas and the acid, an alcohol would be perfect. No esterification should occur without an acid catalyst but to be sure I would use isopropanol rather than ethanol as secondary alcohols are slower to esterify. In practice diethyl-ether or even acetone would would work fine except you would observe the ammonium salt precipitation (the salt would not be soluble in these polar but non-protic solvents).
I think water is just more convenient as you can mesure the pH in it (which is necessary here) and it is not that hard to get rid of if you directly distil the mixture. Also even if it is possible to bubble ammonia gas though a mixture, it's a bit more tedious than just using a water solution.

Mike Master - 2020-04-13

@À fond les ballons I definitely agree with you about having to keep track of the ph. Well, thank you for your informative reply. You sound like you know your chemistry.