Some theory first... (also see previous post)
Post 472609
(Tengo: "SWIM tried the oxidation in bleach, all a...", Novel Discourse)And of course the already mentioned patent
http://l2.espacenet.com/espacenet/bnsviewer?CY=gb&LG=en&DB=EPD&PN=EP1068177&ID=WO+++9952860A1+I+
HOAc + NaOCl -> HOCl + NaAc
APAP + HOCl -> NAPQI + HCl + H2O
HCl + NaAc -> HOAc + NaCl
NAPQI + H2O -> BQ + CH3CONH2 (pH<6)
Summarized:
APAP + NaOCl -> BQ + CH3CONH2 + NaCl (pH<6)
Assuming that HOCl does the oxidation, since it's used to oxidate cyclohexanol in the same way.
SWIM tried this with equimolar amounts of APAP, NaOCl and acetic acid.
15g APAP (unpurified, directly from 30*0,5g tablets)
25ml of 24% acetic acid
150 ml of 5% bleach
Starting at 0°C, slowly adding bleach to the suspension of APAP and acetic acid until the temperature reached 25 °C.
The suspension gets orange immidiately and darkens to orange/brown (brick color) at T+2h.
Another 25ml of 24% acetic acid is added to induce hydrolysis.
At T+5h the reaction has resulted in this:
Brown upper layer and an orange/brown lower layer with white suspended.
These layers are equal in height. If there were an organic layer it should be lower in height since the amount of organic substances are much less than the amount of water.
So it's probably the suspended white that is at the bottom due to gravity.
Adding NaCl (to salt out BQ), nothing visually changes.
Now BQ shouldn't like this polar enviroment and rise to the surface.
Having never seen BQ, SWIM doesn't really know what to look for... MSDS says grey to yellowish-white... Voices at the HIVE say pure BQ is a yellow fluffy powder (and green sparklies when it's contaminated with quinhydrone)
Adding toluene and the suspended white goes to the upper layer.
Probably plenty of unreacted stuff in there (but what, APAP or NAPQI? filler material?).
Adding some HCl and raising the temp (to hydrolize possible unhydrolized NAPQI) and the shit starts polymerizing.
Separating the organic layer and it's reddish-brown...
Conclusion: More or less none (SWIM doesn't now what's in there)
Since HClO is a stronger oxidizing agent than ClO- the equilibrium 2HClO + ClO- <-> ClO3- + 2HCl gets maximally shifted to the right at neutral pH, maybe this affects the reaction.
If it's ClO- and not HOCl that manages to oxidize APAP, then maybe a neutral or acidic reaction isn't the way to go.