Chemgineer
Hazard to Others
Posts: 174
Registered: 25-5-2021
Member Is Offline
|
|
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.
|
|
|
Texium
Administrator
Posts: 4508
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
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…
|
|
|
Texium
|
Thread Moved
6-2-2023 at 12:25 |
blogfast25
International Hazard
Posts: 10562
Registered: 3-2-2008
Location: Neverland
Member Is Offline
Mood: No Mood
|
|
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... 
|
|
|
Texium
Administrator
Posts: 4508
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
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...
|
|
|
Chemgineer
Hazard to Others
Posts: 174
Registered: 25-5-2021
Member Is Offline
|
|
| 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
|
|
|
Fery
National Hazard
Posts: 990
Registered: 27-8-2019
Location: Czechoslovakia
Member Is Offline
|
|
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
International Hazard
Posts: 10562
Registered: 3-2-2008
Location: Neverland
Member Is Offline
Mood: No Mood
|
|
Ouch. Rookie mistake, my bad.
The paintstripper I took apart years ago was based on DCM (CH2Cl2)
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
