6dthjd1
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Chrlorination of napthalene
In late September or early October 2012 I chlorinated naphthalene labeled mothballs using calcium hypochlorite and hydrochloric acid and naphthalene.
The calcium hypochlorite reacts with the naphthalene to give off mainly dichlorine with water vapor and dioxygen as impurities.
In those days glassware was scarce so a teaspoon full of Ca(OCl)2 was added in teaspoon amt. to muriatic acid and the rubber hose was quickly sealed
to the container while I held my breath. IIRC I did this several times spaced out by several minutes but not more than 10 times. No TCCA was not
easily accessible to me back then but I probably didn't look very hard.
I let this sit alone after a few hours IIRC and I saw an oily liquid on top of a waxy flat solid that was off-white.
No catalyst was knowingly added.
Would I be correct to believe that 1-chloronapthalene and 2-chloronapthalence were the majority of the oily layers while the solid part was unreacted
napthalene. I don't remember how many mothballs I added but it was probably no more than 5.
I know more complex chloronapthalenes can form but seeing other threads here indicates they form with heat more favorably
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Pumukli
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Although the envisioned reaction pathway is a bit sketchy, but yes, probably those were in the oily layer, the 1-, and 2-chloronaphthalenes.
Did you find the remnants of the reaction today or why is the sudden interest? 
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6dthjd1
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Quote: Originally posted by Pumukli  | Although the envisioned reaction pathway is a bit sketchy, but yes, probably those were in the oily layer, the 1-, and 2-chloronaphthalenes.
Did you find the remnants of the reaction today or why is the sudden interest?
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I remember many of the early reactions in my mind randomly from time to time.
I was over the past two years slowly going over my early chemistry remannts.
But also the early reactions from 2010-2012 were so special to me because they were some of my first attempts and was from a unique time in my life.
Sometimes I was scared or knew I was doing something people thought of as deviant so there was a cool factor as well. Like when I chlorinated sulfur
at 16
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