malvaxman (Hive Bee)
11-23-01 10:56
No 239714
      Benzyl chloride  Bookmark   

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?
(Old P2P Cook)
11-23-01 11:26
No 239717
      Re: Benzyl chloride  Bookmark   

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.
(Chief Bee)
11-23-01 11:27
No 239719
      Re: Benzyl chloride  Bookmark   

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

2 Toluene + Ca(OCl)2 => 2 Benzyl chloride + Ca(OH)2
11-23-01 13:57
No 239742
      Re: Benzyl chloride  Bookmark   

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 ?
(Distinctive Doe)
11-23-01 15:39
No 239766
      Re: Benzyl chloride  Bookmark   

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

Do Your Part To Win The War
(Hive Bee)
11-23-01 16:33
No 239793
      Re: Benzyl chloride  Bookmark   

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