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. Texium - 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…blogfast25 - 6-2-2023 at 13:03
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... Texium - 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:
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! lolFery - 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.blogfast25 - 7-2-2023 at 02:27
