My Notes
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This literature discussion was inspired by a talk given by Dr. Nora Radu, recipient of the 2025 ACS Award for Distinguished Service in the Advancement of Inorganic Chemistry. It is a bit 'big picture' in nature in that the hydrocyanation reaction is important for the synthesis of nylon. As such, there is a significant amount of background material relating to nylon-6,6. Students will read an article from C&EN, portions of a patent, and portions of an article from J. Chem. Educ. There is also an opportunity to work the classic 'nylon rope trick' demonstration into this literature discussion.
| Attachment | Size |
|---|---|
| Questions for students | 25.1 KB |
| Lit Disc Hydrocyanation 2025.pdf | 406.43 KB |
In this literature discussion students will
- learn about the preparation of nylon-6,6 which will include some 'big picture' concepts.
- read through portions of a patent.
- relate hydrocyanation to the preparation of nylon-6,6.
- examine the hydrocyanation mechanism.
- practice using the CBC method of electron counting for a variety of Ni compounds.
- determine the impact of alkene isomerization on the catalytic efficacy for hydrocyanation.
- explore the steric and electronic impact of various phosphites on catalytic efficacy.
There are certainly a variety of ways to use part of this literature discussion. The J. Chem. Educ. article does an excellent job of explaining the results of several papers and as such, it should probably not be readily available for students to read. That is why there is a handout proposed (it requires copying and pasting figures from this paper) at the end of the questions. The original figures in this paper track electron counts, so they must be modified before being distributed to students. Certainly the questions on the catalytic cycles from this paper (17-26) could stand alone as questions on a problem set or an exam. However, this author sees value in discussion the context of why hydrocyanation is important. The nylon rope trick is certainly not a necessary component, but it is fairly unique to include a relevant demonstration in an upper division course. There is likely more that could have been mined from the patent, but this is a challenging read for undergraduates, and it was felt that dipping their toes into the water was a better approach.
Evaluation
I used this in my senior inorganic course in the fall of 2025. I knew going into it that the timing would not be right as we wouldn't have gotten to reaction mechanisms yet. However, we did have a pretty good conversation. The students seemed to like the big picture aspect of the C&EN article. As I anticipated, the patent was "scary" to them. There is a lot of legalese so certainly pointing to specific sections to read was a good decision. We skipped over most of the reaction scheme materials, but still found plenty to discuss. I will move this later in the semester next year and I think it will be even better.
Stay tuned