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.

Reference:

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

http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VT3-4417B74-7&_user=1111158&_coverDate=10%2F31%2F2001&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000051676&_version=1&_urlVersion=0&_userid=1111158&md5=134ddc1e32bad7c5451eae0214db6d94

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?
>
>
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>Peter Lazarski
>National Grid USA
>Lab. & Testing Svcs., Bldg. 1
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>Liverpool, NY 13088
>(315)460-2114
>-----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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