A quick check of the Merck Index for benzaldehyde says its made

synthetically "... by oxidation of toluene"; benzyl alcohol "by the

Cannizzaro reaction from benzaldehyde + KOH". Was the toluene supposed

to have been reagent grade or another purity? Any possibility it was

left over or recovered from work performed 6 to 20 years ago? Also, how

was it stored? 



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-----Original Message-----

From: DCHAS-L Discussion List [mailto:DCHAS-L**At_Symbol_Here**LIST.UVM.EDU] On Behalf Of

Elizabeth Gregory

Sent: Monday, July 09, 2007 4:04 PM

To: DCHAS-L**At_Symbol_Here**LIST.UVM.EDU

Subject: [DCHAS-L] Toluene? A peroxide former?!


Hi everyone,

 

Our department finally opened up a 5 gallon metal drum of toluene

earlier

this summer. The drum is somewhere between 6 and 20 years old (you can

imagine why I wanted to see it used up...).

 

After a couple of days of "what the %**At_Symbol_Here**&# is this reaction by-product?!",

we've finally figured out that the toluene itself has the following

impurities: benzaldehyde, benzyl alcohol, and benzyl hydroperoxide(!!!).

The

total concentration of these impurities is about 240 mg/L of solution.

 

Has anyone ever heard of toluene forming these products while it's left

sitting around unopened? This is a new one, both to me and our resident

organic chemist.

 

Elizabeth Gregory

Laboratory Manager

Department of Chemistry

SUNY College at Brockport

Room 230 Smith Hall

Brockport, NY 14420

(585) 395-2210

Fax: (585) 395-5805

Email: egregory**At_Symbol_Here**brockport.edu

 


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