Succinimide from Succinic acid
ฝัง
- เผยแพร่เมื่อ 10 เม.ย. 2020
- 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 - วิทยาศาสตร์และเทคโนโลยี
![MOBYE - มีใจทำไมไม่จีบ (ASAP) [Official MV]](http://i.ytimg.com/vi/dCOdz92FU18/mqdefault.jpg)
the fact that I go this whole video without making one *SUCC* joke is honestly a tragedy
Yeah it succs
How many layers of irony are you on?
Yellow chem succs :D
Succ
I would talk about how much your reaction succccced but that would really blow
So I'll keep my dsl's closed
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There I did it for you
Don’t you dare clean anything. The whole “trailer park meth lab” look is part of the charm of the channel.
No matter how much I clean, there's always more mess elsewhere. We ain't ever going to run out of mess
Extractions&Ire I appreciate the reassurance.
Agreed! At least my can rest easy now
it's his aesthetic lol
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.
Tom: don’t request videos of me painting
Also Tom: Lofi hip hop beats to relax/paint benches to
"Should've sanded it all back, everbody's going to say that"
Yes, you should've'd
The TH-cam audience is basically my conscience, who I often chose to ignore
@@ExtractionsAndIre and then paint it white with organics rich paint ;)
if ya gonna go back n sand it, you might as well bog n re-sand for a mint finish
The only crack shack used for actual chemistry
I guarantee you there are many more crack shacks that are used for actual chemistry!
*The only crack shack used for *LEGAL* chemistry. Don't be dissing the meth cooks out there
Hey, making drugs is chemistry!
"It looks red on camera" no, it looks yellow. And we all know what that means.
Yellow chem bad.
Oh no... It's all coming together!!
All yellow chemistry is TRASH
Adam Azra
not so! Yellow chem is either toxic, explosive but generally stinks something awful and stains everything it touches! My
Secret obsession!
I've no idea what it means xD
Tom: "Ammonia is my least favorite gas to deal with"
Me: _nervously glances over at Hydrazoic acid_
Ah yes, enslaved explosive
I mean, to be fair, it's my least favourite gas that I would just release in the room and be like 'this is unpleasant' rather than doing anything about it lol
Ah yes, explosive cyanide
Show Fluorine some love
@@Peter_Schluss-Mit-Lustig Ah yes, the chemist's nemesis: Extremely toxic, extremely reactive.
That 6% recovery from subliming onto an rb flask hurt a little
I felt it in my bones
@@ExtractionsAndIre I think that's actually from the various fumes you produce in the shed :)
You should re-title this video to "Finally Painting the Desk".
That's really the main content, painting with a little bit of chemistry
I came to say this :D
@@infectedrainbow funny
Some of the shots in this were really cool! I really liked the recrystallization and the shot of all three states of succ at the same time.
Very intertwining to watch!
Thanks! I enjoyed filming this!
if it's yellow and it works, it's actually orange™
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.
Glad I can help, good luck with it all, I believe in you!
Don't believe it, Jonas! He said that to me -- now I have no friends and all my glassware is stained YELLOW.
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.
@@jonasgilch3721 Still studying chemistry? Or has the dreaded yellow seeped into the last bits of your sanity and driven you towards a blissfully unexciting career in accounting?
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.
I like your neutralization and reacidifcation technique because it involves little to no math
Hey congratulations on the clean bench!
Oh and congrats on the chemistry thing, whatever that was.
It really felt like an achievement honestly
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
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!
Any update? How did it go?
@@ReaperUnreal I graduated and now I work in engineering plastics research in at one of the largest plastic manufacturing companies in the world. :)
@@TrojanCommander That's awesome, congrats!
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.
WWI weapons smelt like chlorine.
now nilered does all his work in a several million dollar lab that's part of an office building
Maybe you should have stripped off the old paint. If only you had some sort of agent to do than with...
Hmmmmmmmmmmmm
Stripping paint is a waste of good DCM 😅
Yeah. I know for a fact he's still got those ampoules of bromine.
@@AsymptoteInverse Yeah, maybe just bleach the table.
A nice thick coat of "touch powder" would take care of the old paint, and give you a rich brown finish.
Have you considered that the trouble you have in determining the ph is due to your use of YELLOW yest strips?
This
The bubbles in your paint job are from applying too much paint too quickly, trapping vapour boys inside when the outer layer drys. To prevent, you need to do thinner layers of paint and just do more of them!
Ok thank you!!
This is the comment I came here for.
For the bench you need to first scrape all the old paint off with a "painters tool". If there is anything soaked into the wood use a heat gun and towels to wipe it away. Then progress upward in sandpaper grit from 60 to 320, wipe clean with mineral spirits. Paint. Job done.
The part where you painted the bench and the whole screen became white and clean purified my soul Tom.
"It's going yellow"
Me: *Nervousness intensifies*
I've recently found that using ammonium bicarbonate is a great alternative for neutralizing acids with ammonia. You can actually weigh it out and there's way less water to boil off
Hey, thats a great thought
In labs, I used recently N-Bromosuccinimide to synthesise 4-bromomethyl benzoïc acid, which has been used in a Wittig Reaction between a phosphonium ylide and a aldehyde to form 4-vinylbenzoic acid
It was pretty fun ahah
We then passed our 4-bromomethylbenzoic acid trough MRI and it was very pure. There was no other trace of reagent or side product :)
"Dilute heat"
Using a sand bath would save your glassware. My favourite channel.
Sand baths are so slow oh man. But yeah, they do break glassware less...
@@ExtractionsAndIre Can be very thin so the heating is fast (60 or 70 grams) as long as you have indirect heat.
@@abroquet2189 What kind container is good for sand baths? I have some pyrex dishes I just wasn't sure how much heat they can handle.
@@crabraptorjesus I would not recommend kitchenware for heating generally, but it should be okay for sand baths. Any lab glass is suitable if you have a round bottomed flask or uneven surface that will reduce heat transfer. Sand will help create a flat surface and it retains heat very well. Place it on aluminium foil then you have insulation as well, improving efficiency.
Watching you paint that unstripped, unsanded bench hurt a little.
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.
Wow, the music during the timelapses is sooo nice. And the synthesis too of course
Aphex Twin
"If you watch this Channel for a wile, you might know that i am not good at cleaning and keeping promises"
Hmmm...
So grateful for your videos! Needed to make succinimide for Gabriel synthesis for thesis work and this is great. Keep on being awesome and making synthesis accessible to the rest of us
Hey! Ive binged your entire channel. Love the chemistry and keep up the good work!
Glad you like the vids mate!
Get an electric sander will make your life way easier whenever you want to re do the tables
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!
Thank you so much for these uploads, m8. It's really helping us get through lab withdraw during quarantine ;___;
Finally a new video!
You're one of those channels to me that i actually drop everything else when i see they uploaded.
I demand either a video or a live stream dedicated to painting the table.
Ahhh yeah, that cleaning is so satisfying to watch. Good job !
I'm a biochemist. My brain has an entire department dedicated solely to succinate.
Really enjoyed this one, and not just for the painting interludes.
Organic chemistry: the thousand-fold path to black tar.
2:19 Tom: "Looks green in real life but looks red on the camera."
Video: Haha yeah lets make it yellow.
"looks like we might have some glassware down as well as terrible yield - so it's a great day"
Steve Irwin of chemistry right here
*NH3 is my least favourite gas to deal with*
SO2, H2S, HCN: are we a joke to you?
I like H2S lol
@@ExtractionsAndIre yh i mean at least the smell goes away if you poison yourself long enough, a compound with manners
@@nikolashadjipaschalis5629 yeah right?? That's true politeness
Extractions&Ire It’s your friendly neighborhood poisonous gas
Accidentally generated SiH4 almost set my kitchen on fire once.
It can be further simplified
1. add 2 eq. of NH4HCO3 to 1 eq. of succinic acid.
2. gentle heat the mixture with sufficient stirring
3. this will generate ammonium succinate, water and CO2
4. heat the mixture under mild vacuum to remove water
Loved it mate! Really enjoyed it.
If you like Kombucha, I’ve been reusing the brown glass bottles that a lot of that stuff comes in for chemicals. The ones I’ve been buying have HDPE caps so they’re pretty versatile.
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.
Thank you for the nice paint footage! :)
Great to see another one of your videos!
EXTRACT THE SUCC
Loved the video, thank you for this Easter special :)
Bloody yellow chemistry haha
Those benches are lookin great!
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
Would love to see this series revisited
What happened to this project? I was pretty interested in seeing you overcome and eventually succeed!
“Dilute heat” 😂❤ bloody got me this time, another great backyard job, oath keep it up
Yea!! More awesome chemistry videos please.
Big brain time. Don't clean it.
Just break it.
I fricken love this channel
I know little to nothing about chemistry but still enjoy the videos fam, love your stuff!
Timelapse of recrystallizations are just *//chefs kiss//*
I love the painting, that’s who I subscribed.
Wow, you actually did it. You absolute mad lad!
When you said " oh it's going yellow" I was like oh sh*... Something's gone wrong hasn't it 🤣🤣🤣🤣
If you’re planning on making NBS or NCS as a chlorination/bromination agent consider the following:
1,3-Dibromo-5,5-Dimethylhydantoin (DBDMH) itself is a good brominating agent, so I recon the bromochlorodimethylhydantoin you used for the bromine video probably works as is. No need to take the extra step.
I came for the chemistry, I stayed for the bench painting.
What you want to paint that stuff with is a "high hide" primer. Here in the states I use a product called Kilz and I believe its available in Australia. On a side note how much reactive material to you think is stuck in the old paint? Would be neat to see whats "hanging out" on the tables after so many reactions. Anyway love the videos, thanks!
Aw yes! Back on track for the 1-MCP synth!
We will get there!!
enjoyed it. some cool stuff in this one.
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...
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?
@@mikemaster1773 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.
@@afondlesballons881 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.
What is the "overall apple project?" I'm new to this channel.
I think he's trying to make an apple immortal by chemically inhibiting the ripening process.
Yeah! There's a chemical that stops apples ripening, called 1-methylcyclopropene. Theres a playlist of all the videos in this series on my channel
he's making 1-mcp to make immortal apples
I work in emergency medicine and we use succinylcholine as a paralytic for rapid sequence induction for drug assisted intubations. Can you synthesize succinylcholine from this base material?
Next step: paint the benches with chalk paint to give you more room.
Also O O F on the 6% 😂
You always got legit music bro
Make more videos bruh, I’m tryna get through quarantine by watching quality content
I used to always wonder why it looked weird when you boiled stuff, then I remember your upside-down
Woah brother, I signed up for this channel to watch one video every 3 years.
You're thinking of Dougs Lab.....
Yay long vids
Hope for more you are the best
Admit it, you wanted that beaker to crack as soon as you started thinking about cleaning out all that tar.
I won't disagree that I'm very relieved
Ill be succinct. This Succinic acid to Succinimide synthesis video was superbly scintillating!
Yay painting video!
Hey brother..nice !! as soon as I saw Succinimde I immediately thought of a quite long winded procedure to make every gringo's fave marching powder...the ecgonine tricky bit...
When is the next video in this series gonna come?
nice, chemistry and Aphex Twin
The sarcasm is fantastic
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!
I love/hate how youtube autocaption writes out succinimide/succinic acid as a completely different thing *every single time
*
You’re *finally* returning to the 1-MCP experiment!
I'm pretty sure that TCCA would work fine too. You can also make tribromocyanuric acid from cyanuric acid, sodium hydroxide and bromine in water.
Use isopropyl on the surface it dries out the surface and removes oil paint can’t stick to oils sanding isn’t necessary a essential step if you don’t mind a slightly uneven coating.
Chemistry + Humor
Awesome!
Hey mate, I did a bit of research on the isobutene bromination you want to do with NBS, also known as the Wohl-Ziegler reaction. A Scifinder search shows that no one (recently) has done this exact reaction so the reference I'm using is this 1948 review of the by Djerassi, an oldie but I sure it's reliable. Chem. Rev. 1948, 43, 2, 271-317. I'll make some observations on your proposed reaction and summarise what I reckon's relevant from the reference to help you settle on how you want to run the reaction.
1) I feel the most important factor is the low boiling point of isobutene (-7 ºC). Maybe do a sealed tube reaction if you have the appropriate glassware that can handle the pressure or settle on reaction conditions that will work even when the solution is cooled in an ice bath to avoid all your isobutene from evaporating after an hour and ending up with another single digit yield (lol). If you have access to journal articles and want to dig deeper I'd start with a search on low temperature Wohl-Ziegler reactions.
2) Another important consideration is how to remove side-products and by-poducts. 1-Propene, 3-bromo-2-(bromomethyl)- as result of overbromination b.p. ~71 ºC can be removed by distillation, succinimide forms as an insoluble solid in most solvents and can be filtered off or removed by doing a liquid-liquid extraction with water (succinimide is super soluble: 0.33g/mL) since I don't think water would react with your target compound.
3) I'd also suggest looking into the stability of the bromoisobutene. Probably want to store it in a fridge with some foil over it and use it quick to be on the safe side.
4) The NBS should be pure: "N-Bromosuccinimide is prepared in 75-81 per cent yield by brominating quickly an ice-cold, alkaline solution of succinimide . It is desirable to employ N-bromosuccinimide of 97 per cent purity or better in the Wohl-Ziegler reaction and for that purpose, the reagent is best recrystallized quickly from hot water. In the absence of light and moisture, the reagent is stable for many months."
5) There is precedent for this reaction with many solvents: "By far the most widely used solvent has been carbon tetrachloride, which was
employed almost exclusively by Ziegler in his original studies. In certain cases benzene has added advantages, particularly since N-bromosuccinimide is appreciably more soluble in benzene than in carbon tetrachloride. Benzene is not attacked by N-bromosuccinimide in the presence of peroxide under ordinary circumstances. Petroleum ether and heptane have been used occasionally. Chloroform has given excellent results particularly in large-scale runs since it is a more general solvent for organic compounds than carbon tetrachloride... Ethanol, ether and acetone have been used with Nbromoacetamide... X-bromosuccinimide seems to be unstable in it as well as in ethyl acetate, dioxane, and tri-n-butylamine. In many instances no solvent is used and the reaction is carried out in an excess of the reactant."
6) "Dry reagents are essential to avoid hydrolysis of the N-bromoimide." So dry whatever solvent you use!
7) Stoichiometry is not a critical consideration here, isobutene or NBS as limiting reagents have their pros and cons: "In general, no definite rules can be established and the optimum proportions vary often with the specific example at hand."
9) The reaction is typically done at the b.p. of the solvent or higher in order to avoid long reaction times: "Thus, while the bromination of 1-phenyl-1-propene required about 15 hr. in refluxing carbon tetrachloride solution, the reaction was complete almost instantaneously and without appreciable diminution in yield when carried out at 140°C"
10) The reaction can be catalysed by light in the visible spectrum, peroxides and strong lewis acids such a aluminium, zinc, ferrous chloride and these are progressively harsher condition that are used for unreactive molecules, but i don't think they'll necessary here. You could try them if it doesn't work the first time.
11) Djerassi gives a general procedure and it's good to get a sense of the whole process so I'll include the whole section: "Dry reagents are essential to avoid hydrolysis of the N-bromoimide. In general, the reactant is dissolved in carbon tetrachloride or another suitable solvent, N-bromosuccinimide or N-bromophthalimide is added, and the mixture is refluxed. The disappearance of the insoluble N-bromoimide on the bottom with the simultaneous formation of the insoluble imide floating on top indicates the completion of the reaction. This can be confirmed by testing for the absence of bromine (starch-iodide test). Quite often, e.g., in the case of ketones (19), a color develops in the beginning which disappears suddenly when the reaction is complete. This has also been observed in other instances (5, 86). After the completion of the reaction, the insoluble imide is filtered, washed with solvent, and the filtrate is worked up in a suitable manner (removal of solvent, followed by crystallization, distillation, etc.) to isolate the product. The proper conditions will have to be chosen for each particular case, taking into consideration the remarks made in Section III, A to E. In general the reaction is carried out first without catalysts and if unsuccessful (owing to incomplete reaction or other reasons), peroxide or light or both (43) can be employed as catalysts. A combination of several variables may be considered to achieve selectivity or minimize side reactions (c/. 54). The wide variety of experimental conditions which can be used are rather obvious and represent a particularly attractive feature of the Wohl-Ziegler reaction. In many instances, the resulting bromo compound is unstable and loses the elements of hydrogen bromide spontaneously on longer refluxing (c/. 50, 51, 53). In those cases where loss of hydrogen bromide is only partial, the succinimide is filtered at the end of the reaction (negative potassium iodide test, absence of heavy precipitate on the bottom), the solvent is removed and a base is added to complete dehydrobromination; potassium or sodium acetate (5, 38), sodium carbonate (13), dimethylaniline (49, 51, 56), pyridine (c/. 19, 64, 82), collidine (10, 21, 45a, 54), alumina (81), and similar reagents have been used. It should be noted that in particularly unstable bromo compounds, where dehydrobromination occurs before bromination is complete, hydrogen bromide can liberate free bromine from N-bromosuccinimide and give rise to side reactions (97)"
If you reply with the conditions you end up settling on after considering this stuff, I'd be happy to have a look and give it a second opinion :).
Good luck man.
hey man, these are some great thoughts.
The low boiling point of the substrate is something I didn't think enough about when designing this new procedure. Honestly, I'm now not convinced it'll work okay. Doing the reaction under pressure is pretty darn scary and not something i'm set up for.
Someone from my discord (Zabbie, full credit here) found this reference, which is also pretty scary, but very interesting and is perhaps the way I will go forward. pubs.acs.org/doi/abs/10.1021/jo00822a021
It makes the succinimide synth pretty pointless, but hey, it will keep forever, and perhaps another project in the future will actually lend itself much better to a Wohl-Ziegler reaction
@@ExtractionsAndIre Yeah looks good, the paper you linked does the chlorination of isobutene and it looks like it uses readily available chemicals. Never seen NCl3 being used, that'll be cool!
excited for another post
It's all pretty circle-closing chemistry from where I'm sat.
I really enjoy these videos. I slept through my biology/chemistry classes because the teacher didn’t teach. He’d just hand out packets of busy work, say figure it out and fuck off back to MySpace.
18:17 beautiful crystalls!
I hear caro's acid works well for cleaning up tar.
Is it legal to buy toluene just as is in your place? I cant find any near mine, i wonder why..