Date: Tue, 10 Jul 2007 15:32:35 -0400
Reply-To: David Erickson <erickson**At_Symbol_Here**MSU.EDU>
Sender: DCHAS-L Discussion List <DCHAS-L**At_Symbol_Here**LIST.UVM.EDU>
From: David Erickson <erickson**At_Symbol_Here**MSU.EDU>
Subject: Re: Toluene? A peroxide former?!
In-Reply-To: <7FCB95300E34CD46831A79E87C3B148A8E55B0**At_Symbol_Here**NYHCBMSG04.NA.NGRID .NET>

Benzyl alcohol is a peroxide former as reported in this excellent 
reference on peroxides.  Does it make sense that ppm solvent 
impurities can form ppm levels of peroxide?

Weird case. Good luck.


Peroxides and peroxide-forming compounds
Donald E. Clark
Available online 19 September 2001.

David E. Erickson,
Senior Industrial Hygienist
Michigan State University
Office of Radiation, Chemical & Biological Safety
C-124 Research Complex-Engineering

At 12:31 PM 7/10/2007, Lazarski, Peter M. wrote:
>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?
>The information contained in this e-mail message and any attachments may
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>Peter Lazarski
>National Grid USA
>Lab. & Testing Svcs., Bldg. 1
>7437 Henry Clay Blvd.
>Liverpool, NY 13088
>-----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
>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(!!!).
>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**
>This e-mail and any files transmitted with it, are confidential to 
>National Grid and are intended solely for the use of the individual 
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