DCHAS-L Archives, Jul 19 2019 - Re: [DCHAS-L] Safer Diels-Alder reaction

I’m in industry, rather than academia. I have had to train non-chemists to handle chemicals. I often run against the “What’s in it for me?” syndrome… if the activity is not just risky enough to care, then people won’t care to learn proper handling techniques and other safety protocols.

I’m reminded of my analytical chem lab involving cyanide and titration. The professor didn’t seem to particularly like giving us the experiment, but he knew the technique was an important one and we needed to learn how to handle it. Now… 16yrs later, I don’t recall everything about that experiment, but I do recall all of the safety precautions around working with cyanide solutions.

Both of you have a point… it needs to be safe enough for a large group, but risky enough for people to put in the effort to learn respect for chemicals and proper handling.

Good luck!

Thank you,

Yaritza Brinker

260.827.5402

From: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU> On Behalf Of Harry Elston
Sent: Friday, July 19, 2019 12:15 PM
To: DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: Re: [DCHAS-L] Safer Diels-Alder reaction

** External Email **

Kendra,

All chemicals can be handled safely and the Diels-Alder reaction has been around for about 90+ years, so those with a strong organic chemistry background should have the experience in reaction control. What better place to teach chemical safety and how to handle exothermic reactions than in a highly-supervised classroom with limited quantities and good containment?

Chemistry is not a “zero-risk” occupation and we, as educators, should not imply that it is. It is a risk-managed occupation. A well-equipped academic laboratory is ideally suited for risk management. I would encourage you not to miss a great opportunity to teach safety to the next generation.

Best,

Harry

From: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU> On Behalf Of Denlinger, Kendra
Sent: Friday, July 19, 2019 9:41 AM
To: DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: [DCHAS-L] Safer Diels-Alder reaction

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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