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ParadoxChem126
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[*] posted on 7-4-2013 at 21:19
Phenol from Domestically Available Chemicals


I have not yet had a chance to try this synthesis, but I have come up with the procedure. Start by reacting a quantity of aspirin (acetylsalicylic acid) with saturated aqueous sodium hydroxide solution (crystal drain opener) until it is all dissolved. The aspirin may contain binders that do not dissolve, so simply filter the solution. The solution will consist of sodium salicylate and sodium acetate. Now, slowly add concentrated hydrochloric acid (hardware store muriatic acid) in small amounts. Keep adding HCl until no more salicylic acid precipitates out. Acetic acid will have formed as a byproduct, but it will stay in solution. Filter out the salicylic acid, wash it with water, and set it aside to dry.

Once the salicylic acid is dry, put 25g of it into a suitable round-bottom flask and clamp the flask to a ring stand. Now, heat the salicylic acid with a hot torch for 5-6 seconds at a time, pausing 10-15 seconds between heating sessions. Continue to heat and pause for a total of 10-15 minutes. During the heating, the salicylic acid will break down into phenol and carbon dioxide gas. After heating, allow the flask to cool to room temperature, and add 100ml of dichloromethane (distilled from paint stripper). Swirl the flask until all of the phenol is dissolved. Now set up for distillation and distill off the dichloromethane at 40 degrees Celsius. When all of the dichloromethane is removed, the residue in the boiling flask will be composed of phenol with a purity of 95 to 98%.

[Edited on 8-4-2013 by ParadoxChem126]

[Edited on 8-4-2013 by ParadoxChem126]

[Edited on 8-4-2013 by ParadoxChem126]

[Edited on 8-4-2013 by ParadoxChem126]

[Edited on 9-4-2013 by ParadoxChem126]
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Nicodem
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8-4-2013 at 11:34
vmelkon
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[*] posted on 8-4-2013 at 17:55


I think you could do a decarboxylation reaction with the salicyclic acid.

Heat solid salicyclic acid with solid NaOH to 500 °C or something like that. You should end with phenol and Na2CO3.
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ParadoxChem126
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[*] posted on 8-4-2013 at 18:06


Well, if you heat the molten phenol to 500 degrees Celsius, won't it all instantly vaporize? Also, I would not want to mess with molten sodium hydroxide and phenol vapors...
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Finnnicus
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[*] posted on 8-4-2013 at 18:48




[Edited on 9-4-2013 by Finnnicus]




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macckone
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[*] posted on 8-4-2013 at 21:17


Certain throat sprays also contain phenol.
It might make an interesting work-up to isolate the phenol.
Chloraseptic
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ParadoxChem126
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[*] posted on 8-4-2013 at 21:26


Yeah, but the ingredients list phenol as 1.4%. You would only be able to isolate a very small amount from the entire bottle. Still might be interesting to try…
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[*] posted on 8-4-2013 at 21:36


Quote: Originally posted by vmelkon  
I think you could do a decarboxylation reaction with the salicyclic acid.

Heat solid salicyclic acid with solid NaOH to 500 °C or something like that. You should end with phenol and Na2CO3.

I hope you have a steel container for that molten NaOH.
Isn't phenol deathly toxic?
I hope that decomposition of salicylic acid works - I'd love a good source of phenolphthalein.




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[*] posted on 9-4-2013 at 06:59


Quote: Originally posted by ParadoxChem126  
Yeah, but the ingredients list phenol as 1.4%. You would only be able to isolate a very small amount from the entire bottle. Still might be interesting to try…

That comes to about 2.4g per bottle.
If you want cheap go the benzene sulfonate route or cumene hydroperoxide method.
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[*] posted on 9-4-2013 at 07:07


Quote: Originally posted by elementcollector1  

Isn't phenol deathly toxic?

In large quantities, breathing hot phenol gas or getting hot phenol on your skin is inadvisable. Of course the same can be said for steam and boiling water. It is somewhat toxic but certainly not as toxic as hydrochloric acid. If exposed to vapor, seek medical attention. If you get it on your skin wash it off and seek medical attention if there is skin damage. If it is hot and you get it on your skin, it will cause severe burns. Small quantities are used as a throat medication, so I wouldn't freak out if I got a speck of dust on my arm. Of course, if you get a little sulphuric acid on your arm it will leave a mark.
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[*] posted on 9-4-2013 at 07:43


Quote: Originally posted by macckone  
Quote: Originally posted by elementcollector1  

Isn't phenol deathly toxic?

In large quantities, breathing hot phenol gas or getting hot phenol on your skin is inadvisable. Of course the same can be said for steam and boiling water. It is somewhat toxic but certainly not as toxic as hydrochloric acid. If exposed to vapor, seek medical attention. If you get it on your skin wash it off and seek medical attention if there is skin damage. If it is hot and you get it on your skin, it will cause severe burns. Small quantities are used as a throat medication, so I wouldn't freak out if I got a speck of dust on my arm. Of course, if you get a little sulphuric acid on your arm it will leave a mark.


Actually a speck of phenol on your arm it is absorbed and will cause burns and blistering. It is quite toxic actually. More so than HCl...
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[*] posted on 9-4-2013 at 13:55


Quote: Originally posted by elementcollector1  
Quote: Originally posted by vmelkon  
I think you could do a decarboxylation reaction with the salicyclic acid.

Heat solid salicyclic acid with solid NaOH to 500 °C or something like that. You should end with phenol and Na2CO3.

I hope you have a steel container for that molten NaOH.
Isn't phenol deathly toxic?
I hope that decomposition of salicylic acid works - I'd love a good source of phenolphthalein.


The decomposition of salicylic acid should work... Check out this website about phenol from salicylic acid.
http://books.google.com/books?id=y5mZrW1KB_AC&pg=PA129&a...

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[*] posted on 9-4-2013 at 17:34


http://www.youtube.com/watch?v=hlR3UWLyxEU

Don't know how difficult these chemicals are to acquire. But, in my day if you needed Phenol you either bought it outright, or made it from Aniline. Or, if you were a Chem student, you Nitrated Benzene, Reduced the Nitrobenzene it to Aniline.....Etc.

Aspirin seems like an interesting alternative.
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[*] posted on 9-4-2013 at 18:45


Benzene and nitric acid are not easily accessible to me, so I've kind of ruled out the aniline approach. Also, I don't have a fume hood, and I don't want to mess with benzene without one.
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[*] posted on 10-4-2013 at 09:19


I can verify that the OP's procedure works, at least sort of, I have done it personally a while back with 2 failures and 1 success. I believe the failures took place because I do not have a Bunsen burner I was using a propane torch, held at a distance of course, so the heat applied was never consistent. I used chloroform in the place of DCM. I was thinking about doing a YouTube video since none exist on the topic but I haven't had a chance to improve the dependability.



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[*] posted on 10-4-2013 at 10:07


Maybe you could obtain cumene and try using the cumene process in a Hock rearrangement to obtain acetone and phenol. Acetone is always useful. :cool:



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[*] posted on 10-4-2013 at 16:57


Well, Benzene is a carcinogen.......eventually. A few minor exposures are unlikely to give you the big C... Everybody, used to get lots of Benzene exposure, all of the time. Most of us are just fine.

Aniline can also be prepared by the degradation of Benzamide. A material you could likely produce from Benzoic Acid, or Sodium Benzoate. These are materials that can be obtained cheaply, and in bulk.

[Edited on 11-4-2013 by zed]
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[*] posted on 19-4-2013 at 13:35


Quote: Originally posted by ParadoxChem126  

The decomposition of salicylic acid should work... Check out this website about phenol from salicylic acid.
http://books.google.com/books?id=y5mZrW1KB_AC&pg=PA129&a...



Wow, that is very simple. Just heat the salicyclic acid.
The text suggests to use methylene chloride (DCM, CH2Cl2) which I don't have but I guess other solvents would do the job as well.
In the USA, you can buy BBQ cleaner liquid and distill to get the CH2Cl2 out.

[Edited on 19-4-2013 by vmelkon]
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[*] posted on 4-5-2013 at 21:24


I think that distilling it from paint stripper is cheaper.



[Edited on 5-5-2013 by ParadoxChem126]
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[*] posted on 30-9-2013 at 18:09


Phenol, a quite toxic chemical but damn I love its smell xD!

I can confirm that the decarboxylation of salicylic acid does in fact work. The first minute after you put the flame out a strong smell of phenol is perceptible. Later I made the extraction using ethyl acetate and apparently it worked just fine. Recristalization was made later using water as the solvent. You can get very pure fenol from this method (pure enough as to what a home chemist can ask for)

I do apologize for not having any photograph of the other processes; this was actually taken by a friend of mine.

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[*] posted on 30-9-2013 at 22:10


Theres a fairly detailed experimental over at Versuchschemie
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[*] posted on 1-10-2013 at 11:45


Quote:

Actually a speck of phenol on your arm it is absorbed and will cause burns and blistering. It is quite toxic actually. More so than HCl...


Not true
HCl LD50 oral (human) 2.8mg/Kg
Phenol LD50 oral 270mg/Kg

Phenol is not as toxic as most of the stuff we take for granted.
If it were that toxic it wouldn't be in Chloraseptic.
Having said that, take reasonable precautions because it can be dangerous but then so can potassium chloride.

[Edited on 1-10-2013 by macckone]
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[*] posted on 1-10-2013 at 12:37


So, is anyone here agreeing with the OP regarding producing the salicylic acid from aspirin tablets? Because honestly, producing phenol from aspirin tablets sounds way easier than the other methods mentioned here such as trying to screw around with benzene, etc. I understand there might be purity issues from binders in aspirin tablets, but at that, pure aspirin is itself a fairly simple synth. However, one has to come by acetic anhydride for that, and thus, simply generating the salicylic acid from aspirin tablets becomes a bit more desirable for me.

Also, the step involving the dichloromethane is simply a recrystallization, correct? One should have crude phenol simply from heating the salicylic acid, and this crude phenol should be solid once it cools to room temp?

[Edited on 1-10-2013 by MichiganMadScientist]
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[*] posted on 1-10-2013 at 13:55


I have found one study about chlrobenzoic acid synthesis from hypochlorite and benzoic acid and then probably hydroxybenzoic acids may be obtained from them with NaOH, they could be used instead of aspirin for decarboxylation.
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[*] posted on 1-10-2013 at 14:30


@Macckone: Where did you get that data from? Its way off according to Sigma:

HCl (gas) LD50 Oral (Rabbit) 900 mg/kg

Phenol LD50 Oral (Rat) 410-650 mg/kg, LD50 Dermal (Rabbit) 630 mg/kg

Phenol is pretty nasty stuff. Its hepatotoxic (liver) and sufficiently volatile to cause concern. I've seen a bottle where half the contents were in the upper part of the bottle due to sublimation.

The crude phenol can be (vacuum) distilled to purify to an acceptable level (again, see the VC page).

[Edited on 1-10-2013 by DJF90]
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[*] posted on 2-10-2013 at 05:24


Quote: Originally posted by DJF90  
Theres a fairly detailed experimental over at Versuchschemie
Provide the link, then.



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