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DCHAS-L Discussion List Archive

From: Sandra Koster <sandrakkoster**At_Symbol_Here**GMAIL.COM>
Subject: Re: [DCHAS-L] Safer Diels-Alder reaction
Date: Sat, 20 Jul 2019 08:16:02 -0500
Reply-To: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU>
Message-ID: CAG9vrO458WoZOg+=QOg76DenGA5O=57DWqivRQrSAmjk25izUg**At_Symbol_Here**mail.gmail.com
In-Reply-To


I googled "greener diels alder reaction" and got a hit from the Royal Society of Chemistry on an in situ preparation of cyclopentadiene from its dimer and reaction with maleic anhydride and other dienophiles. Solvent free in a "thermodynamically controlled reaction". This lists D. Huertas et al as authors from the journal "Green Chemistry" circa 2009. There were other hits on the search as well. This certainly sounds better than cracking dicyclopentadiene and transferring it. If you haven't worked with that you might not know how truly obnoxious the smell is, disregarding other hazards.

Sandra Koster
Senior lecturer, emeritus
University of Wisconsin-La Crosse

On Fri, Jul 19, 2019, 9:57 AM Denlinger, Kendra <denlingerk**At_Symbol_Here**xavier.edu> wrote:
Hello everyone,
I'm teaching an organic lab right now (my first time teaching this course), and we're supposed to do a Diels-Alder reaction in a few weeks. It's a reaction between cyclopentadiene and maleic anhydride, and the students are supposed to "crack" dicyclopentadiene to cyclopentadiene using a distillation with mineral oil, and then react cyclopentadiene with maleic anhydride in ethyl acetate (which is a very exothermic reaction). Long story short, the whole thing sounds like an accident waiting to happen.

I know there has got to be a safer (and maybe even greener!) Diels-Alder reaction out there for organic lab students, but I don't know exactly where to look and thought maybe it would be a good question for all of you! I don't have a long time to search and test things, so if someone has a Diels-Alder procedure you use at your university that works and is safer, I would love to hear about it!

Thanks for any assistance!
Kendra Denlinger

Kendra Leahy Denlinger, Ph.D.

Adjunct Faculty

Department of Chemistry

Xavier University

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