nitration of phenol

Irene

Irene
Hi the world of knowledge,

The Btec lot have just finished the practical "The nitration of phenol"......omg it smells like TCP. Any ideas on how to clean the round bottomed flask that contains the black oily sludge (Which has now solidified). It's in the fume cupboard and the teachers are complaining!!

Irene
 

007

COMMITTEE
Hi the world of knowledge,

The Btec lot have just finished the practical "The nitration of phenol"......omg it smells like TCP. Any ideas on how to clean the round bottomed flask that contains the black oily sludge (Which has now solidified). It's in the fume cupboard and the teachers are complaining!!

Irene
Depending on the technique you followed you need to be very careful with what you've produced. If you didn't carry out the nitration at a low temperature, for example, in ice you would have caused further nitration to occur - as OH is an electron donating group this means that the NO2 group will have further nitrated into the 2,4,6 position on the ring which will make 2,4,6-trinitrophenol - which is more commonly known as picric acid, which is a banned substance in schools as it is highly explosive and has an antiseptic aroma. You may well have made some of this, if so seeing as you won't have stored it at a cold temperature I suggest a call to CLEAPSS, ASAP.
 
Depending on the technique you followed you need to be very careful with what you've produced. If you didn't carry out the nitration at a low temperature, for example, in ice you would have caused further nitration to occur - as OH is an electron donating group this means that the NO2 group will have further nitrated into the 2,4,6 position on the ring which will make 2,4,6-trinitrophenol - which is more commonly known as picric acid, which is a banned substance in schools as it is highly explosive and has an antiseptic aroma. You may well have made some of this, if so seeing as you won't have stored it at a cold temperature I suggest a call to CLEAPSS, ASAP.
An excellent analysis 007.:)
 

Irene

Irene
Depending on the technique you followed you need to be very careful with what you've produced. If you didn't carry out the nitration at a low temperature, for example, in ice you would have caused further nitration to occur - as OH is an electron donating group this means that the NO2 group will have further nitrated into the 2,4,6 position on the ring which will make 2,4,6-trinitrophenol - which is more commonly known as picric acid, which is a banned substance in schools as it is highly explosive and has an antiseptic aroma. You may well have made some of this, if so seeing as you won't have stored it at a cold temperature I suggest a call to CLEAPSS, ASAP.
Thank you for your reply. I have just mentioned it to our teacher who has subsequently decided to cancel the practical. I think the word banned substance and explosive frightened him!!
 

007

COMMITTEE
Thank you for your reply. I have just mentioned it to our teacher who has subsequently decided to cancel the practical. I think the word banned substance and explosive frightened him!!
You still need to sort the results of the practical you previously mentioned, my advice would be to contact CLEAPSS but also keep the contents of the round bottomed flask wet, the contents will be far more unstable when dry ;)
 
Thank you for your reply. I have just mentioned it to our teacher who has subsequently decided to cancel the practical. I think the word banned substance and explosive frightened him!!
We decided to ban the experiment as well, can I ask what experiment will you do instead? Many thanks
 
Depending on the technique you followed you need to be very careful with what you've produced. If you didn't carry out the nitration at a low temperature, for example, in ice you would have caused further nitration to occur - as OH is an electron donating group this means that the NO2 group will have further nitrated into the 2,4,6 position on the ring which will make 2,4,6-trinitrophenol - which is more commonly known as picric acid, which is a banned substance in schools as it is highly explosive and has an antiseptic aroma. You may well have made some of this, if so seeing as you won't have stored it at a cold temperature I suggest a call to CLEAPSS, ASAP.
There is a safer protocol using 4-aminophenol.i would be happy to share it with you.
 
Hi the world of knowledge,

The Btec lot have just finished the practical "The nitration of phenol"......omg it smells like TCP. Any ideas on how to clean the round bottomed flask that contains the black oily sludge (Which has now solidified). It's in the fume cupboard and the teachers are complaining!!

Irene
Warm dilute nitric acid.
 
Thank you for your reply. I have just mentioned it to our teacher who has subsequently decided to cancel the practical. I think the word banned substance and explosive frightened him!!
He and so many others. As a rule of thumb if someone is not confident in what they are doing I would suggest don't do it.
 
We decided to ban the experiment as well, can I ask what experiment will you do instead? Many thanks
If you're looking for a safer nitration experiment, CLEAPSS provide a procedure for one in their document L195: Safer Chemicals, Safer Reactions. For those really into their organic chemistry, it also offers subsequent proecdures for hydrolysis of the ester, then reduction of the nitro group to the amine.
 
Hi the world of knowledge,

The Btec lot have just finished the practical "The nitration of phenol"......omg it smells like TCP. Any ideas on how to clean the round bottomed flask that contains the black oily sludge (Which has now solidified). It's in the fume cupboard and the teachers are complaining!!

Irene
Dilute warm nitric acid.
 
Thank you, I was looking for another reaction to prepare aromatic compound.
We do this with a twist and yes I have to say that I introduced it with my creative talents. We scan the mixture before and after nitration in a UV spectrophotometer across all wavelengths to judge the extent of nitration.
 
I beg to differ as I have done this many times and followed the reaction products with scanning UV.
This may be the case with the reaction, but cleaning out the flask will mean that things are more concentrated as there is no solvent and why risk nitrating further when it will not make things more water soluble? There's risk with little to gain just to clean a flask. The sodium phenolate is certainly more water soluble being a salt.
While using nitric to clean off inorganic residues is fine (all nitrates are soluble) using it for organics is not a good idea.
 
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