I like your “lab manner”, sound like a respectable person who is also responsible, with regards to explaining lab safety and the correct procedures to stay safe.
Thanks for your meticulous videos,. Though i am no chemist i love watching things being made and you you help me better understand the chemistry that is going on. All the best
Let me just say that for the record, I have tried the preparation of methylamine from the acetamide via the Hofmann rearrangement. You need about a litre of NaOCl solution to convert a mere 40ml of Acetamide. The whole process is quite unpleasant and the workup is incredibly time-consuming. You can react the methylamine with HCl, but the separation of the methylammonium chloride and sodium chloride from the bleach is very difficult. I highly recommend the traditional formaldehyde-ammonium chloride preparation.
I would suspect the grind on that short path condenser -I would expect a 24/40 joint to fit tightly enough so that the acetamide wouldn't creep through the joint enough to freeze it up. And I wouldn't suspect that nice Kontes receiving flask. On a good day, you get what you pay for. A very informative and well-made video, however, thank you.
how about a simpler but longer preparation? mixing Aqueous ammonia with Ethyl Acetate and allowing it to sit for a few days until there is no longer two layers. there you have acetamide in good yield which you need to separate by distillation. you can get yield in the 90+ range by gassing the mixture to fully saturate it with ammonia and leaving it for up to a week to fully react.
I have done it by azeotropic distillation with a heavy return mode Dean-Stark apparatus (aka Clevenger) using chloroform as the carrier solvent. Works amazingly well and I dunno why nobody ever suggests it.
Would circulating warm-ish water in the condenser be a good idea? Maybe even water that's close to 100C so the water can pass through but the acetamide would properly reflux? Just an idea.
@@BackYardScience2000 There ya go. Hey BackYard Science 2000 - I love your channel too! haha. Keep it up man. P.S. Does anyone know where Doug went? Dude went MIA a while ago. If he gave up on the whole YT thing I totally respect that, but if its not that then idk. Hope all is well though.
@@jhyland87 Tom from Explosions and Fire said in one of his live streams on the Extractions and Ire channel mantioned he heard from somebody who new Doug that he is fine, like Tom said it might just be the stress of doing TH-cam videos.
I don't see an _acetamide to methylamine via the Hofmann rearrangement reaction_ video on your channel.... I have a feeling it got deleted because _methylamine_ is on the DEAs _super_ naughty chemical list... Sucks :-\ I have a feeling that's happened to a lot of your videos that may have existed before I caught onto your greatness. I wish I had access to them :-\ Feel like I'm missing out on some awesome content.
+Toxi Core "all of your equipment" - will be well over a thousand dollars if quality equipment is purchased, but doable for ~$400 if you know where to look and accept a quality loss, however you can start doing decent o-chem with $200-300 if you buy the absolute bare minimum.
I found a basic organic chemistry glassware set on ebay to get my glassware collection going, I spent $79 bucks. I can vouch for this seller and this particular item. www.ebay.com/itm/lab-glassware-kit-24-40-primary-Organic-chemistry-glassware-kit-lab-glassware/161249151847?hash=item258b32cb67:g:h1oAAOSwwbdWKSHh
@@beanlets Formamide isn't very toxic, the only real risk is that in presence of certain acid catalysts, or by pyrolysis, formamide dehydrates to HCN. Also the reaction works for propionic acid and IIRC benzoic acid, but I don't think it works for formic acid. Don't quote me on that though it's been years since I looked into this. Anyway heating ammonium formate will produce formamide. Or ammonolysis of methyl formate.
That will make ammonium acetate and water. If the ammonium acetate is heated strongly it will decompose into acetamide, but this would require temperatures high enough to decompose the acetamide that is produced into carbon monoxide and ammonia and potentially small amounts of methylamine. Furthermore, if the ammonium acetate is heated just a little too much, it will break down into hydrogen cyanide and water (especially in the presence of transition metal catalysts), which can pose a significant risk. The method shown here is much more convenient, efficient, and far less dangerous.
I wonder if you could use catalytic hydrogenation of formamide with that pyrophoric nickel catalyst you made to get that chemical you mentioned. Just a thought.
Methylamine is a gas so it wouldn't work very well. Just imagine trying to pump the hydrogen in and separate the outcoming methylamine... Sounds like a toxic nightmare...
@@williamackerson_chemist To separate the outcoming methylamine you'd simply need dry NaOH packed in a drying tube, a gas bubbler, some 80% warm formic acid and maybe glass wool. Easiest separation ever. However if you have access to a vacuum pump, pyrophoric nickel and formamide i bet that you also have access to aqueous formaldehyde and ammonium chloride. Way more straightforward, clean and cost effective.
mattibboss I use this one. (Sorry it is all in english) www.amazon.com/Glass-Thermometer-Adapter-Chemistry-Glassware/dp/B01LPFDKU0/ref=sr_1_11?s=industrial&ie=UTF8&qid=1540139531&sr=1-11&keywords=24%2F40+thermometer+adapter
lol Look were the take off is. It is about the boiling flask and not the receiver. And he is not talking about a propelled vessel but a exploding one in some way.
You still alive Doug? It's been a while
I like your “lab manner”, sound like a respectable person who is also responsible, with regards to explaining lab safety and the correct procedures to stay safe.
Thanks for your meticulous videos,. Though i am no chemist i love watching things being made and you you help me better understand the chemistry that is going on. All the best
Let me just say that for the record, I have tried the preparation of methylamine from the acetamide via the Hofmann rearrangement. You need about a litre of NaOCl solution to convert a mere 40ml of Acetamide. The whole process is quite unpleasant and the workup is incredibly time-consuming. You can react the methylamine with HCl, but the separation of the methylammonium chloride and sodium chloride from the bleach is very difficult. I highly recommend the traditional formaldehyde-ammonium chloride preparation.
I'd like to see the reaction pathway with phosphorous pentasulfide.
I would suspect the grind on that short path condenser -I would expect a 24/40 joint to fit tightly enough so that the acetamide wouldn't creep through the joint enough to freeze it up. And I wouldn't suspect that nice Kontes receiving flask. On a good day, you get what you pay for. A very informative and well-made video, however, thank you.
how about a simpler but longer preparation? mixing Aqueous ammonia with Ethyl Acetate and allowing it to sit for a few days until there is no longer two layers. there you have acetamide in good yield which you need to separate by distillation. you can get yield in the 90+ range by gassing the mixture to fully saturate it with ammonia and leaving it for up to a week to fully react.
a week bubbling ammonia in a solution?
Finally new video !!
nice work
You use that acetamide to create methylamine? I don't recall seeing a methylamine video?
Whats the best way to dry the acetic acid before hand for this reaction? Sieves? Magnesium sulfate?
Sieves are generally sensitive to acids
@@natejl772 oh that's right, duh.
You can dry commercial 80% acetic acid with Na2SO4, then distill, optionally with some conc. sulfuric acid added. MgSO4 might also work for this.
@@bromisovalum8417 really?... Wasnt aware of that. I may try it out..
I have done it by azeotropic distillation with a heavy return mode Dean-Stark apparatus (aka Clevenger) using chloroform as the carrier solvent. Works amazingly well and I dunno why nobody ever suggests it.
I learn a ton - thank you.
Can i use vinigar 5% instead of the glacial???
Since the acetamide melts at 79C couldn't the freezing problem be solved by running near-boiling water or steam through the condenser?
Would circulating warm-ish water in the condenser be a good idea? Maybe even water that's close to 100C so the water can pass through but the acetamide would properly reflux? Just an idea.
That's a better idea than I suggested, I just suggested running water at the end of the night to melt it back down.
Chemplayer did this in their synthesis. They heated the water to around 80°c I think.
@@BackYardScience2000 There ya go.
Hey BackYard Science 2000 - I love your channel too! haha. Keep it up man.
P.S. Does anyone know where Doug went? Dude went MIA a while ago. If he gave up on the whole YT thing I totally respect that, but if its not that then idk. Hope all is well though.
@@jhyland87 Tom from Explosions and Fire said in one of his live streams on the Extractions and Ire channel mantioned he heard from somebody who new Doug that he is fine, like Tom said it might just be the stress of doing TH-cam videos.
@@synthesizer8026 oh thats good then. Yeah im tempted to start making YT videos, but i hear its very stressful.
I don't see an _acetamide to methylamine via the Hofmann rearrangement reaction_ video on your channel.... I have a feeling it got deleted because _methylamine_ is on the DEAs _super_ naughty chemical list... Sucks :-\ I have a feeling that's happened to a lot of your videos that may have existed before I caught onto your greatness. I wish I had access to them :-\ Feel like I'm missing out on some awesome content.
Yeah I was looking for same !
What's the actual usage though? Diethyl oxalate & urea will give urethane (former clinical hypnotic). doi:10.1002/aoc.1629
how much did all of your equipment cost? i am curious because i am planning to build my own lab
+Toxi Core
"all of your equipment" - will be well over a thousand dollars if quality equipment is purchased, but doable for ~$400 if you know where to look and accept a quality loss, however you can start doing decent o-chem with $200-300 if you buy the absolute bare minimum.
I found a basic organic chemistry glassware set on ebay to get my glassware collection going, I spent $79 bucks. I can vouch for this seller and this particular item.
www.ebay.com/itm/lab-glassware-kit-24-40-primary-Organic-chemistry-glassware-kit-lab-glassware/161249151847?hash=item258b32cb67:g:h1oAAOSwwbdWKSHh
A lot
Check out Deschem on ebay
Once you start getting into chemistry the costs never stop because you end up wanting to do every reaction possible.
Boiling point or melting point of your final product? (As a measure of purity)
Hey Doug. Can you make methylamine in a video sometime?
Maybe if he comes back from the dead
@@jumpierwolf is he dead?
@@mattiadarioli774 dead as in "he hasn't uploaded", no idea if something actually happened to him
would this work with 95% formic acid and urea to make formamide?
Saftey , especially with the high toxicity of formamide (carbonyl amine) is mandatory but maybe.
@@beanlets Formamide isn't very toxic, the only real risk is that in presence of certain acid catalysts, or by pyrolysis, formamide dehydrates to HCN. Also the reaction works for propionic acid and IIRC benzoic acid, but I don't think it works for formic acid. Don't quote me on that though it's been years since I looked into this. Anyway heating ammonium formate will produce formamide. Or ammonolysis of methyl formate.
Why not neutralize AcOH with NH4OH???
That will make ammonium acetate and water. If the ammonium acetate is heated strongly it will decompose into acetamide, but this would require temperatures high enough to decompose the acetamide that is produced into carbon monoxide and ammonia and potentially small amounts of methylamine. Furthermore, if the ammonium acetate is heated just a little too much, it will break down into hydrogen cyanide and water (especially in the presence of transition metal catalysts), which can pose a significant risk. The method shown here is much more convenient, efficient, and far less dangerous.
I wonder if you could use catalytic hydrogenation of formamide with that pyrophoric nickel catalyst you made to get that chemical you mentioned. Just a thought.
Methylamine is a gas so it wouldn't work very well. Just imagine trying to pump the hydrogen in and separate the outcoming methylamine... Sounds like a toxic nightmare...
@@williamackerson_chemist
To separate the outcoming methylamine you'd simply need dry NaOH packed in a drying tube, a gas bubbler, some 80% warm formic acid and maybe glass wool. Easiest separation ever.
However if you have access to a vacuum pump, pyrophoric nickel and formamide i bet that you also have access to aqueous formaldehyde and ammonium chloride. Way more straightforward, clean and cost effective.
can you give me exact name and maybe link for that thermometer type k adapter thingy?? (im from Germany...so free shipping maybe?)
mattibboss
Look at this on eBay www.ebay.com/itm/191813486034
Not the thermometer, the glass abapter so i can stick the thermometer in
You need a glass tube and then seal the top off
mattibboss I use this one. (Sorry it is all in english) www.amazon.com/Glass-Thermometer-Adapter-Chemistry-Glassware/dp/B01LPFDKU0/ref=sr_1_11?s=industrial&ie=UTF8&qid=1540139531&sr=1-11&keywords=24%2F40+thermometer+adapter
There are better ways to methylamine, but this reaction would be neat for propionamide and subsequently ethylamine.
There was No danger of "Blowing out the flask" - It is Not a closed system. The Shortpath has a vacuum takeoff.
lol Look were the take off is. It is about the boiling flask and not the receiver. And he is not talking about a propelled vessel but a exploding one in some way.
when you say equal weights.. do you mean equal molar weights?
acetic acid and urea both have a molar mass of 60, in this case equal weights is the same as equimolar
15:25 Warm liquid goo phase.
What are the uses of acetamide?
+Alkaios "It finds some use as a plasticizer and as an industrial solvent." -Wikipedia
+Alkaios you can use it as an H2S donor.
+Joschimido this is the case with thioacetamide ;)
+Alkaios Pentaerythritol can be made with it.
***** maybe.
i thincked why acetic acid is precursor and is restricted, i find anwer :))
Acetamide smells like mice.
Not really. I find it smells more like rice...
Acetamice , acetamide
A very good video with a well presented synthesis.