Did you add any base to the paba? I thought of the sodium benzoate+NaOH rxn but use paba instead would give aniline but in your video you apparently don't add any base is this correct?
I just googled it and apparently you are the first person to actually do this rxn. Have U come across any posts/comments/references or anything like that of someone who has actually done this before?
One of the reasons I wanted to film this was because I hadn't seen it done before and it's practically useful for the amateur chemist. I started looking into this reaction about two years ago after running the decarboxylation of niacin to pyridine, I figured that a similar thing could be done for paba to aniline. I was unable to find any papers using simple thermal decarboxylation of paba but I did find similar papers demonstrating the thermal decarb of anthranlic acid to aniline here: cdnsciencepub.com/doi/pdf/10.1139/v52-065 In early 2019 first tried decarboxylation in aqueous H2SO4 but I only got a tiny yield of what I presumed to be aniline from its immiscibility in water and subsequent solubility in acid. Moving onto thermal decarb, I then figured that I may as well try just heating the solid before experimenting with adding Cu chromite or anything else. To my surprise, I found that simple thermal decarb yielded an oily liquid with chemical and physical properties corresponding to aniline. I've used the aniline from this to make quinoline and phenylhydrazine which I then made into tetrahydrocarbazole in another video, also the product has a hypergolic reaction with nitric acid. My procedure has been replicated by a number of people on Explosions&Fire's discord server as well.
@@corrosion-chem- Great synth and videos. I was wondering if have ever done any GC/LC/TLC/MS analytics on your synthesized compounds to measure purity and contaminants from side reactions?
Very nice. Did you add a stabilizer or were you using it quickly? Something like hydroquinone or tert-butylcatechol? Also did you ever check the concentration? I think this method is a good solution for me I am just curious how it worked out for you in the end?
I didn’t add any stabilizer, just stored the aniline in an amber bottle away from light, over time the aniline will darken regardless. I didn’t do a titration to determine the exact concentration/purity but it should be quite pure after distillation. Many other people have replicated my procedure (there are some other videos posted about this reaction on RU-vid now) and they have had good results as well!
06:13 is it ok that aniline trapped to your vacuum pump? Your oil in the pump will be contaminated and will release toxic aniline into atmosphere... after adsorbing water from air during non-use storage of the pump it will later lead to lowering maximum vacuum achievable with this pump. And vacuum pump oils is not dirty cheap to replace it every day.
you would most likely have to react the aniline HCl with iodine and nitric acid. There‘s really a lot to be found, even on eikipedia, so you should probably go there yourself to find the best way
@@giansieger8687 You can also start from vitamin B10, form the silver salt and react it with excess iodine. This reaction is the Hunsdieker decarboxylation. There are many variations on this method but all replace a carboxyl group with a halogen group.
