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Author: Subject: Benzyl alcohol from paint stripper
Chemgineer
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[*] posted on 6-2-2023 at 12:03
Benzyl alcohol from paint stripper


I bought some paint stripper which on the MSDS confirmed mainly benzyl alcohol and also that is was a water based product. It is a gel gloopy sort of liquid.

I transferred it to a bound bottom flask and carried out a simple distillation and at around 100 deg C I got a white cloudy distillate then the temperature rose to ~200 deg C and I got a heavier clear liquid which I captured in a separate flask.

What I've noticed though is that when I leave it overnight it takes on a yellow colour and then this eventually become orange. I can distil it again at around 200 deg C and get a clear solution again leaving behind a red liquid. However i've done this 3 times now and it keep changing colour so I figure something is going on.

Maybe i'll react it with HCL to produce benzyl chloride, recrystalise this and then use sodium hydroxide to hopefully make better benzyl alcohol.
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[*] posted on 6-2-2023 at 12:25


Really, recrystallize benzyl chloride? A powerful lachrymator with a melting point of -39°C? Doesn’t sound like you’ve thought this through too well…



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[*] posted on 6-2-2023 at 13:03


Quote: Originally posted by Chemgineer  

Maybe i'll react it with HCl to produce benzyl chloride, recrystalise this and then use sodium hydroxide to hopefully make better benzyl alcohol.


Apart from what Texium said, reacting with HCl may not be so easy because the alcohol is a primary one.

Easier probably to esterify to (e.g.) the acetate. Smells very nice apparently... :cool:




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[*] posted on 6-2-2023 at 13:21


Actually, that part isn’t far fetched at all. Since the substitution is occurring at a benzyl position, the carbocation intermediate is far more stable than a primary carbocation would normally be, and it is able to undergo SN1 substitution quite easily. See here:

https://www.sciencemadness.org/whisper/viewthread.php?tid=71...




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[*] posted on 6-2-2023 at 13:33


Quote: Originally posted by Texium  
Really, recrystallize benzyl chloride? A powerful lachrymator with a melting point of -39°C? Doesn’t sound like you’ve thought this through too well…


You got me bang to rights, more research needed before speaking my mind! lol
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[*] posted on 6-2-2023 at 21:48


Benzyl alcohol has m.p. -15 C so you can probably freeze it in a common freezer which operates at -18 C. But it may stay liquid due to supersaturation as the T difference is only 3 C. E.g. I let acetic acid (m.p. +15 C), dioxane (m.p. +12 C) in fridge at +4 C and after weeks they were still liquid. But both froze in freezer at -18 C and then I moved them from freezer into fridge +4 C. I let acetic acid in garage at +10C and after months it was still liquid, but after pouring a little of mixture of crystals + acid into it, the content started to crystallize as crystal seeds were introduced into supersaturated solution.
Benzyl alcohol has very nice smell like roses.
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[*] posted on 7-2-2023 at 02:27


Quote: Originally posted by Texium  
Actually, that part isn’t far fetched at all.


Ouch. Rookie mistake, my bad.

The paintstripper I took apart years ago was based on DCM (CH2Cl2)




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