Benzyl chloride

[malvaxman]

U.S. Pat.#1,280,612

Toluene and dry bleaching powder are heated together to 105 degrees in the abscence of other reagents.This avoids by-product formation. If equal amts are used, volume-wise, there is a high conversion. If more bleaching powder is used, the conversion is more robust, but contaminants such as benzal chloride and benzotrichloride are formed...

-----------------------------------------------------

What is "bleaching powder"? It must contain chlorine, is it PbCl2?

[terbium]

According to the Merck Index, "bleaching powder" is also known as "chlorinated lime" and contains a mixture of Ca(OCl)2, CaCl2, Ca(OH)2 and water. The Merck goes on to say that "Commercial products usually range between 24% and 37% of available chlorine.

I would say that the calcium hypochlorite available from swimming pool supply stores would be a substitute.

[Rhodium]

Ca(OCl)2 aka Calcium Hypochlorite aka Pool Shock.

2 Toluene + Ca(OCl)2 => 2 Benzyl chloride + Ca(OH)2

[timsong]

This sounds a nice simple method, and it saves generating chlorine to gas the toluene with (other method).

A few questions:-

Does the reaction vessel need cooling or is it done under reflux ?

Does Ultra Violet light need to be present for the reaction to proceed ?

Does a completly glass bottle need to be used to store benzyl chloride or are some plastics ok ?

I have heard that benzyl chloride has a lachrymatory effect, just how bad at room temp ?

[foxy2]

UV is very BAD!!!!!!!!!!!!
Heard that causes explosions in this reaction.


Do Your Part To Win The War

[lugh]

malvaxman & timsong, see

Post 35459

(CHEM_GUY: "Re: benzyl chloride from hypochlorite salts", Chemistry Discourse) and

Post 36700

(CHEM_GUY: "Re: benzyl chloride from hypochlorite salts", Chemistry Discourse) then see Bozakium's

Post 239653 (missing)

(Bozakium: "Re: vaccum pump oil substitutue", Chemicals & Equipment) for some good advice