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Plastics are all around us in materials that are used daily. Due to their usefulness, plastics are widely produced, but estimates suggest that only 9% of plastic has been successfully recycled. Much of the rest of the plastic end up in landfills and oceans where it can release toxic substances. Even for plastics that can be recycled, it is usually cheaper to make new plastic than to recycle used plastic. A more sustainable plastics economy would use closed-loop recycling, but few materials are amenable to this type of process.
This research aimed at measuring thermodynamic parameters of self-immolative poly(glyoxylamides), which represent a class of materials that can be readily depolymerized and potentially recycled. Understanding these parameters will aid in designing new recyclable materials.
The research started with synthesizing the monomer 2-oxo-2-(pyrrolidin-1-yl)acetaldehyde. This aldehyde was prepared through a sequence of three reactions. While we were able to successfully prepare the target monomer, we found that the compound was extremely hygroscopic: it rapidly reacts with water, to form a hydrate that is unable to undergo the target polymerization reaction. We examined a number of different strategies to remove water and found that using a Dean–Stark reaction could afford the aldehyde monomer in approximately 90% purity. However, even the small amount of water remaining was enough to impede successful polymerization. Future studies could explore more methods for purifying the target monomer or alternate strategies to access the target polymer via post-polymerization modification to enable measuring the thermodynamic properties.
Despite the challenges we encountered, I was able to learn a lot of new skills such as running organic reactions under inert atmosphere, performing 1H and 13C NMR spectroscopy, and analyzing spectral data. I was also glad to be able to put to practice my Organic Chemistry knowledge from my classes.
