In my previous video I described how to extract acetylsalicylic acid from Aspirin tablets. In this video, I will be hydrolyzing ester bond in the acetylsalicylic acid to form salicylic acid.
For any of you, unfortunate enough to not have a vacuum filter and your product to be yellow. You can simply dry it as much as you can then place it into a beaker or Pyrex dish (dry), wrap aluminium foil over the top to block it and then put it on a stove for low heat. Once it heats up, the salicylic acid will sublime against the surface and on the foil. You will have nice pure needle like fibre crystals which you can scrape off
I wanna see a video where you extract salicylic acid or whatever from willow or some other plant source and convert it into aspirin, and talk about how you would explain how ancient people could've done the process, or how you would tell/teach them the process to turn salicylic acid from plants into aspirin.
I attempted this myself and after the reflux, the solution became an orange juice colour which then caused my product to be orange Any ideas of why this may of happened?
Strong solutions of NaOH can etch glass slowly if heated very strongly. NurdRage has some videos on this in his series where he makes sodium metal. In this case it shouldn't be a major problem.
with an excess of water, after the sodium reaction, couldn't one add acetic acid to neutralize the sodium, and since there's an excess of water and hydroxide ions it would continue the hydrolisis of the sasylic and keep it from forming acesasylic? basically, what other acids could be used instead of hlc?
Why are you refluxing the reaction, I thought that was only necessary during an acid hydrolysis? Shouldn't a base hydrolysis happen almost immediately?
a thing that i do not understand is that when I follow this process verbatim it all seems to behave a little different. for example, when i add the base solution it is all completely dissolved with no stirring whatsoever. and in later steps when using a short path for distilling the final product everything distills at a much much lower temp then it should. Now i have done this 8 or ten times using various brands of aspirin and its always the same., also, i have done this part of the process in a beaker one time. simply dissolved the. acetylsalicylic acid in a base solution allowed to cool then acidified it with no reflux and yields were the same
+Clown Whisper Hmm very interesting. Sometimes things don't go exactly as planned. As long as your final product is good, then there is nothing to worry about
+Mr.chang cooler Not really. I can't think of any reasonable way and I didnt find much when I googled it. Its more plausible to go the other way, from toluene to phenol.
Nile Red Yeah, i've read oxidizing toluene will create phenol. Then is there any way to remove the hydroxyl to create benzene? From there i've read adding chloromethane to benzene would get you toluene
+Mr.chang cooler I would use iodomethane instead of chloromethane because it's easiser to make. also, you need to activate the ring with AlCl3, which isn't the easiest to come by. Removing the OH from phenol will be too hard to be worth it. It is much easier to just decarboxylate sodium benzoate or benzoic acid (I did a video on sodium benzoate decarboxylation). In the future, I do plan to make iodomethane and make some toluene. However, in general, benzene is harder to get, so I find it a little wasteful to convert it to toluene! If you look hard, you should be able to find a decent amount of toluene.
+Shadowphyre Not really. I have a video on how I did it, but it is kind of the only way. There might be another way using a high boiling solvent, but it won't be nearly as easy.
th-cam.com/video/A0e0BDEE4Ic/w-d-xo.html I dont fully do all the distillations though. I should have done 1 or 2 more. But I was told I couldn't continue in the lab on it, ha.
Right now, I am not working in a lab at all, so I can't. I will be in the lab again starting January. If you can remember, you can request it then :p. Also, I technically do decarboxylations for the both of the cadaverine/putrescine synthesis videos. Unless you mean specifically decarboxylation of salicylic acid.
never saw a temperature or deration?? what am i supposed to google the boiling point of NaOH?? The boiling point of an 80% sodium hydroxide (NaOH) aqueous solution is around 298°C (568°F)
For any of you, unfortunate enough to not have a vacuum filter and your product to be yellow. You can simply dry it as much as you can then place it into a beaker or Pyrex dish (dry), wrap aluminium foil over the top to block it and then put it on a stove for low heat. Once it heats up, the salicylic acid will sublime against the surface and on the foil. You will have nice pure needle like fibre crystals which you can scrape off
Is it safe to use for cosmetic purposes upon dilution?
I wanna see a video where you extract salicylic acid or whatever from willow or some other plant source and convert it into aspirin, and talk about how you would explain how ancient people could've done the process, or how you would tell/teach them the process to turn salicylic acid from plants into aspirin.
How do you know when the reflux process (the one that yields disodium salicylate) reaches completion?
Nice job
I attempted this myself and after the reflux, the solution became an orange juice colour which then caused my product to be orange
Any ideas of why this may of happened?
what is the procedure for the acid cat hydrolysis?
Doesn't NaOH decompose glass when you reflux with it? or is that only at excessively high temperature and under very concentrated conditions?
Strong solutions of NaOH can etch glass slowly if heated very strongly. NurdRage has some videos on this in his series where he makes sodium metal. In this case it shouldn't be a major problem.
Pro tip: don't mix the solid chemicals then add water all at once; bad things happen
with an excess of water, after the sodium reaction, couldn't one add acetic acid to neutralize the sodium, and since there's an excess of water and hydroxide ions it would continue the hydrolisis of the sasylic and keep it from forming acesasylic?
basically, what other acids could be used instead of hlc?
tested with 20% phosphoric acid; crystals precipitate almost immediately
whats the temperature during the hydrolysis
Can you make acetylsalicylic acid (aspirin) from salicylic acid in an other video? (the reverse of this reaction)
Bump
It's total waste
Can you use calcium hydroxide? I have quite a bit of it, and want to use it for something.
Probably not as calcium hydroxide is almost insoluble in water
Why are you refluxing the reaction, I thought that was only necessary during an acid hydrolysis? Shouldn't a base hydrolysis happen almost immediately?
I just got a real good deal on one pound of salicylic acid for 10 bucks~!
woot woot
3:18 he is there! :D
Cool
a thing that i do not understand is that when I follow this process verbatim it all seems to behave a little different. for example, when i add the base solution it is all completely dissolved with no stirring whatsoever. and in later steps when using a short path for distilling the final product everything distills at a much much lower temp then it should. Now i have done this 8 or ten times using various brands of aspirin and its always the same.,
also, i have done this part of the process in a beaker one time. simply dissolved the. acetylsalicylic acid in a base solution allowed to cool then acidified it with no reflux and yields were the same
+Clown Whisper Hmm very interesting. Sometimes things don't go exactly as planned. As long as your final product is good, then there is nothing to worry about
I'm curious, is there a way to replace the OH group on the phenol with a CH3 group to form toulene?
+Mr.chang cooler Not really. I can't think of any reasonable way and I didnt find much when I googled it. Its more plausible to go the other way, from toluene to phenol.
Nile Red Yeah, i've read oxidizing toluene will create phenol. Then is there any way to remove the hydroxyl to create benzene? From there i've read adding chloromethane to benzene would get you toluene
+Mr.chang cooler I would use iodomethane instead of chloromethane because it's easiser to make. also, you need to activate the ring with AlCl3, which isn't the easiest to come by.
Removing the OH from phenol will be too hard to be worth it. It is much easier to just decarboxylate sodium benzoate or benzoic acid (I did a video on sodium benzoate decarboxylation).
In the future, I do plan to make iodomethane and make some toluene. However, in general, benzene is harder to get, so I find it a little wasteful to convert it to toluene! If you look hard, you should be able to find a decent amount of toluene.
Nile Red Ah. Thank you for the input :)
How can you turn the salicylic acid into phenol as you said in the video? Is there any easy way that does not involve distillation?
+Shadowphyre Not really. I have a video on how I did it, but it is kind of the only way. There might be another way using a high boiling solvent, but it won't be nearly as easy.
+Nile Red could you link the video please?
th-cam.com/video/A0e0BDEE4Ic/w-d-xo.html
I dont fully do all the distillations though. I should have done 1 or 2 more. But I was told I couldn't continue in the lab on it, ha.
thanks you
+Nile Red One more question.Is the salicylic acid toxic ?Like 2-3 grames is going to do any bad to your body?
what lab are you working in and what do you do?
+marcel fernandez watch the previous video he goes through the whole process step by step.
he uses 500 tablets.
can-you-make-tramadol-from-salicylic-acid
What is the molarity of the HCl solution ?
Mohamad Massalha 10-12 should work
Can you make a video on decarboxilation?
Right now, I am not working in a lab at all, so I can't. I will be in the lab again starting January. If you can remember, you can request it then :p. Also, I technically do decarboxylations for the both of the cadaverine/putrescine synthesis videos. Unless you mean specifically decarboxylation of salicylic acid.
does this work with KOH too?
***** ok thanks, (i thought that but weren't too sure because of difference in the metal itself or the pKb)
It's working with KOH ?
is there way to hydrolyse cellulose at home?
How many tablets were used?
It's in the previous video; 500 325mg tablets
how do you decarboxylate phenol
i mean salicylic acid
ok this is the second video you have on pre cursors for improvised explosives
we did the opposite of this in lab class 😁
refluxing this hydrolysis does not seem necessary
never saw a temperature or deration?? what am i supposed to google the boiling point of NaOH?? The boiling point of an 80% sodium hydroxide (NaOH) aqueous solution is around 298°C (568°F)
libbta 5:37